BMF 83 - Antidepressants | v1 | 10/20

Antidepressants

Depression is a common psychiatric disorder impacting millions of people worldwide. It is caused by an imbalance of chemicals in the brain, namely serotonin and noradrenaline1. Everyone experiences highs and lows, but depression is characterised by persistent sadness for weeks or months2. With depression there is lasting feeling of hopelessness, often accompanied by anxiety. Depression is usually treated with a combination of counselling and drug therapy. There is also evidence that exercise can help depression. Most people with moderate or severe depression benefit from antidepressant medication. There are a wide range of antidepressants on the market, which can be broadly divided according to mechanism of action3; • Selective serotonin reuptake inhibitors (SSRIs) • Serotonin-norepinephrine reuptake inhibitors (SNRIs) • Serotonin modulator and stimulators (SMSs) • Serotonin antagonist and reuptake inhibitors (SARIs) • Norepinephrine reuptake inhibitors (NRIs or NERIs) • Tetracyclic antidepressants (TeCAs) • Tricyclic antidepressants (TCAs) • Monoamine oxidase inhibitors (MAOIs)

Today the most common first choice of medication is a SSRI1, i.e. Citalopram, Escitalopram, Fluvoxamine, Paroxetine, Sertraline, Fluoxetine. Antidepressants are not addictive, but can result in With depression there is lasting withdrawal symptoms when feeling of hopelessness, often therapy is stopped. These include stomach upset, flu-like accompanied by anxiety. symptoms, anxiety, dizziness, Sufferers lose interest in things vivid dreams or electric shock that they previously enjoyed, sensations. In most cases and experience bouts of symptoms are quite mild, and do not persist more than a tearfulness. Rational thinking week or two, but occasionally and decision making are they can be quite severe. impacted. Physical manifestations Onset occurs very soon after stopping, and so can be include tiredness, insomnia, differentiated from depression loss of appetite and sex drive, relapse, which tends to occur aches and pains2. At its later2. worst depression can cause the sufferer to feel suicidal. References: [1] A. W. Jones, Perspectives in Drug Discovery: A collection of Essays on the History and Development of Pharmaceutical Substances. National Board of Forensic Medicine. RMV Report – 2010:1. [2] NHS Choices Your health, your choices, Clinical depression http://www.nhs.uk/ Conditions/Depression/Pages/Introduction.aspx (accessed August 16). [3] Wikipedia – Key search terms ‘antidepressants’ ‘depression’ ‘SSRI’ (accessed August 2016). Antidepressants product listing

Chiron No. Structure Name CAS Agomelatine O

HN 11892.15 Agomelatine 138112‐76‐2 O

O D HN D D 14027.15 Agomelatine‐d3 (acetamide‐2,2,2‐d3) 1079389‐38‐0 O

Amitriptyline

2543.20 HCl Amitriptyline hydrochloride 549‐18‐8

N

HCl 10343.20 Amitriptyline‐d3 hydrochloride (N‐methyl‐d3) 342611‐00‐1 D D N D

HCl

D Amitriptyline‐d6 hydrochloride (N,N‐dimethyl‐d6) 203645‐63‐0 11852.20 D N D

D D D

2544.15 Dibenzosuberone (Amitriptyline Imp. A (EP)) 1210‐35‐1

O

2697.20 HCl Cyclobenzaprine hydrochloride (Amitriptyline Imp. B (EP)) 6202‐23‐9

N

2698.19 HCl Nortriptyline hydrochloride (Amitriptyline Imp. C (EP)) 894‐71‐3

NH

HCl 9193.19 Nortriptyline‐d3 hydrochloride (N‐methyl‐d3) 203784‐52‐5

NH

D D D

5‐(3‐Dimethylaminopropyl)‐10,11‐dihydro‐5H‐ 2711.20 1159‐03‐1 HO dibenzo[a,d]cyclohepten‐5‐ol (Amitriptyline Imp. D (EP)) N

Amoxapine NH

N 11992.17 N Amoxapine 14028‐44‐5 Cl O Bupropion O H N Cl 14181.13 Bupropion hydrochloride (Amfebutamone HCl) 31677‐93‐7 HCl

D D O D H D N Cl 14019.13 D HCl (±)‐Bupropion‐d9 hydrochloride (tert‐butyl‐d9) 1189725‐26‐5 D D D D Citalopram F

9397.20 N HBr (±)‐Citalopram hydrobromide 59729‐32‐7 O

N

11330.19 (±)‐Desmethylcitalopram hydrochloride (Norcitalopram HCl) 97743‐99‐2 Chiron No. Structure Name CAS Agomelatine

11892.15 Agomelatine 138112‐76‐2

Chiron No. Structure Name CAS Agomelatine

14027.15 Agomelatine‐d3 (acetamide‐2,2,2‐d3) 1079389‐38‐0

11892.15 Agomelatine 138112‐76‐2

Amitriptyline

2543.20 Amitriptyline hydrochloride 549‐18‐8 14027.15 Agomelatine‐d3 (acetamide‐2,2,2‐d3) 1079389‐38‐0

Amitriptyline

10343.20 Amitriptyline‐d3 hydrochloride (N‐methyl‐d3) 342611‐00‐1

2543.20 Amitriptyline hydrochloride 549‐18‐8

11852.20 Amitriptyline‐d6 hydrochloride (N,N‐dimethyl‐d6) 203645‐63‐0 10343.20 Amitriptyline‐d3 hydrochloride (N‐methyl‐d3) 342611‐00‐1

2544.15 Dibenzosuberone (Amitriptyline Imp. A (EP)) 1210‐35‐1

11852.20 Amitriptyline‐d6 hydrochloride (N,N‐dimethyl‐d6) 203645‐63‐0

2697.20 Cyclobenzaprine hydrochloride (Amitriptyline Imp. B (EP)) 6202‐23‐9

2544.15 Dibenzosuberone (Amitriptyline Imp. A (EP)) 1210‐35‐1

2698.19 Nortriptyline hydrochloride (Amitriptyline Imp. C (EP)) 894‐71‐3

2697.20 Cyclobenzaprine hydrochloride (Amitriptyline Imp. B (EP)) 6202‐23‐9

9193.19 Nortriptyline‐d3 hydrochloride (N‐methyl‐d3) 203784‐52‐5 2698.19 Nortriptyline hydrochloride (Amitriptyline Imp. C (EP)) 894‐71‐3

5‐(3‐Dimethylaminopropyl)‐10,11‐dihydro‐5H‐ 2711.20 1159‐03‐1 dibenzo[a,d]cyclohepten‐5‐ol (Amitriptyline Imp. D (EP)) 9193.19 Nortriptyline‐d3 hydrochloride (N‐methyl‐d3) 203784‐52‐5 Amoxapine

11992.17 Amoxapine 14028‐44‐5 5‐(3‐Dimethylaminopropyl)‐10,11‐dihydro‐5H‐ 2711.20 1159‐03‐1 dibenzo[a,d]cyclohepten‐5‐ol (Amitriptyline Imp. D (EP)) Bupropion Amoxapine 14181.13 Bupropion hydrochloride (Amfebutamone HCl) 31677‐93‐7

11992.17 Amoxapine 14028‐44‐5

14019.13 (±)‐Bupropion‐d9 hydrochloride (tert‐butyl‐d9) 1189725‐26‐5 Bupropion Citalopram 14181.13 Bupropion hydrochloride (Amfebutamone HCl) 31677‐93‐7

9397.20 (±)‐Citalopram hydrobromide 59729‐32‐7 14019.13 (±)‐Bupropion‐d9 hydrochloride (tert‐butyl‐d9) 1189725‐26‐5

Chiron No. Structure Name CAS AgomelatineCitalopram F

11330.19 (±)‐Desmethylcitalopram hydrochloride (Norcitalopram HCl) 97743‐99‐2 N HCl 11892.15 H Agomelatine 138112‐76‐2 9397.20 O (±)‐Citalopram hydrobromide 59729‐32‐7

N F D D 9398.20 D (±)‐Citalopram‐d4 hydrobromide (4‐ uorophenyl‐ d4) 1219803‐58‐3 D N HBr

14027.15 O Agomelatine‐d3 (acetamide‐2,2,2‐d3) 1079389‐38‐0 11330.19 N (±)‐Desmethylcitalopram hydrochloride (Norcitalopram HCl) 97743‐99‐2 F

O Amitriptyline 11631.20 HO (S)‐Citalopram oxalate (Escitalopram oxalate) 219861‐08‐2 OH N O N O

2543.20 AmitriptylineClomipramine hydrochloride 549‐18‐8

N 9530.19 Cl Clomipramine hydrochloride 17321‐77‐6 HCl N 10343.20 Amitriptyline‐d3 hydrochloride (N‐methyl‐d3) 342611‐00‐1

N Cl D 10356.19 D HCl Clomipramine‐d6 hydrochloride (N,N‐dimethyl‐d6) 1189882‐28‐7 D N

11852.20 D D Amitriptyline‐d6 hydrochloride (N,N‐dimethyl‐d6) 203645‐63‐0 D

N 14026.19 Cl Clomipramine‐d3 hydrochloride (N‐methyl‐d3) 1398065‐86‐5 D HCl 2544.15 D Dibenzosuberone (Amitriptyline Imp. A (EP)) 1210‐35‐1 D N

N 10357.182697.20 Cl NorclomipramineCyclobenzaprine hydrochloride hydrochloride (Desmethylclomipramine (Amitriptyline Imp. B (EP)) HCl) 298546202‐‐2314‐‐96

HN HCl

Desipramine

2698.19 Nortriptyline hydrochloride (Amitriptyline Imp. C (EP)) 894‐71‐3 N 11411.18 HCl Desipramine hydrochloride (Imipramine HCl EP Imp A) 58‐28‐6

NH

Dosulepin S 9193.19 Nortriptyline‐d3 hydrochloride (N‐methyl‐d3) 203784‐52‐5

11413.19 HCl Dosulepin hydrochloride (Dothiepin HCl) 897‐15‐4

N 5‐(3‐Dimethylaminopropyl)‐10,11‐dihydro‐5H‐ 2711.20 Doxepin 1159‐03‐1 dibenzo[a,d]cyclohepten‐5‐ol (Amitriptyline Imp. D (EP)) O

Amoxapine 9400.19 HCl Doxepin hydrochloride (cis+trans) 1229‐29‐4

N 11992.17 Amoxapine 14028‐44‐5 O

Bupropion 9399.19 HCl Doxepin‐d3 hydrochloride (N‐methyl‐d3) (cis+trans) 347840‐07‐7 (as trans) D D 14181.13 Bupropion hydrochloride (Amfebutamone HCl) 31677‐93‐7 N D

O

14019.13 (±)‐Bupropion‐d9 hydrochloride (tert‐butyl‐d9) 1189725‐26‐5 10360.18 HCl Nordoxepin hydrochloride (cis+trans) 2887‐91‐4

N H Citalopram Duloxetine

S 10346.189397.20 HCl (±)Duloxetine‐Citalopram hydrochloride hydrobromide 13643459729‐‐3234‐‐79 O N H

Fluoxetine

F F 9760.17 F Fluoxetine 54910‐89‐3 11330.19 (±)‐Desmethylcitalopram hydrochloride (Norcitalopram HCl) 97743‐99‐2 N O H

9291.17 Fluoxetine hydrochloride 56296‐78‐7

9292.17 Fluoxetine‐d5 hydrochloride (phenyl‐d5) 1173020‐43‐3

9402.16 Norfluoxetine hydrochloride 57226‐68‐3 9398.20 (±)‐Citalopram‐d4 hydrobromide (4‐ uorophenyl‐ d4) 1219803‐58‐3

9398.20 (±)‐Citalopram‐d4 hydrobromide (4‐ uorophenyl‐ d4) 1219803‐58‐3

11631.20 (S)‐Citalopram oxalate (Escitalopram oxalate) 219861‐08‐2

Clomipramine 11631.20 (S)‐Citalopram oxalate (Escitalopram oxalate) 219861‐08‐2

9530.19 Clomipramine hydrochloride 17321‐77‐6 Clomipramine

9530.19 Clomipramine hydrochloride 17321‐77‐6

10356.19 Clomipramine‐d6 hydrochloride (N,N‐dimethyl‐d6) 1189882‐28‐7

10356.19 Clomipramine‐d6 hydrochloride (N,N‐dimethyl‐d6) 1189882‐28‐7

14026.19 Clomipramine‐d3 hydrochloride (N‐methyl‐d3) 1398065‐86‐5

14026.19 Clomipramine‐d3 hydrochloride (N‐methyl‐d3) 1398065‐86‐5

10357.18 Norclomipramine hydrochloride (Desmethylclomipramine HCl) 29854‐14‐6

Desipramine 10357.18 Norclomipramine hydrochloride (Desmethylclomipramine HCl) 29854‐14‐6

11411.18 Desipramine hydrochloride (Imipramine HCl EP Imp A) 58‐28‐6 Desipramine

Dosulepin 11411.18 Desipramine hydrochloride (Imipramine HCl EP Imp A) 58‐28‐6

11413.19 Dosulepin hydrochloride (Dothiepin HCl) 897‐15‐4 Dosulepin

Doxepin 11413.19 Dosulepin hydrochloride (Dothiepin HCl) 897‐15‐4

9400.19 Doxepin hydrochloride (cis+trans) 1229‐29‐4 Doxepin

9400.19 Doxepin hydrochloride (cis+trans) 1229‐29‐4

9399.19 Doxepin‐d3 hydrochloride (N‐methyl‐d3) (cis+trans) 347840‐07‐7 (as trans)

9399.19 Doxepin‐d3 hydrochloride (N‐methyl‐d3) (cis+trans) 347840‐07‐7 (as trans)

10360.18 Nordoxepin hydrochloride (cis+trans) 2887‐91‐4

Duloxetine 10360.18 Nordoxepin hydrochloride (cis+trans) 2887‐91‐4

10346.18 Duloxetine hydrochloride 136434‐34‐9 Duloxetine Fluoxetine 10346.18 Duloxetine hydrochloride 136434‐34‐9

Chiron9760.17 No. Structure FluoxetineName 54910CAS‐89‐3 AgomelatineFluoxetine F F 9291.179760.17 F FluoxetineFluoxetine hydrochloride 5629654910‐7889‐73 HCl 11892.15 N O Agomelatine 138112‐76‐2 H D D D 9291.17 Fluoxetine hydrochloride 56296‐78‐7 9292.17 D D Fluoxetine‐d5 hydrochloride (phenyl‐d5) 1173020‐43‐3 F F N O HCl 14027.15 H F Agomelatine‐d3 (acetamide‐2,2,2‐d3) 1079389‐38‐0

F 9292.17 F Fluoxetine‐d5 hydrochloride (phenyl‐d5) 1173020‐43‐3 9402.16 F HCl Norfluoxetine hydrochloride 57226‐68‐3 Amitriptyline O NH2 F F 9402.16 F D D HCl Norfluoxetine hydrochloride 57226‐68‐3 2543.209403.16 NorfluoxetineAmitriptyline‐d5 hydrochloride hydrochloride (propyl‐1,1,2,2,3‐d5) 1185132549‐18‐92‐8 ‐6 O NH D 2 D D Fluvoxamine O N NH2

O 10343.2010347.19 F AmitriptylineFluvoxamine‐d3 hydrochloride maleate (N‐methyl‐d3) 34261161718‐‐8200‐‐91 F HO O F O OH Imipramine

11852.20 N Amitriptyline‐d6 hydrochloride (N,N‐dimethyl‐d6) 203645‐63‐0 10853.19 HCl Imipramine hydrochloride 113‐52‐0

N

Lofepramine 2544.15 O Dibenzosuberone (Amitriptyline Imp. A (EP)) 1210‐35‐1 N

11897.26 Cl Lofepramine 23047‐25‐8 N 2697.20 Cyclobenzaprine hydrochloride (Amitriptyline Imp. B (EP)) 6202‐23‐9

Maprotiline

11898.20 HCl Maprotiline hydrochloride 10347‐81‐6 2698.19 Nortriptyline hydrochloride (Amitriptyline Imp. C (EP)) 894‐71‐3 NH

Meprobamate O O

9468.9 H2N O O NH2 Meprobamate 57‐53‐4 9193.19 Nortriptyline‐d3 hydrochloride (N‐methyl‐d3) 203784‐52‐5

D O D D O

9233.9 H2N O O NH2 Meprobamate‐d3 1185106‐66‐4

5‐(3‐Dimethylaminopropyl)‐10,11‐dihydro‐5H‐ 2711.20 1159‐03‐1 dibenzo[a,d]cycloheptenMianserin‐5‐ol (Amitriptyline Imp. D (EP))

N Amoxapine 9413.18 N HCl Mianserin hydrochloride 21535‐47‐7

11992.17 Amoxapine 14028‐44‐5 D D D N 9414.18 Mianserin‐d3 hydrochloride (methyl‐d3) 1219804‐97‐3 N HCl Bupropion

14181.13 Bupropion hydrochloride (Amfebutamone HCl) 31677‐93‐7 NH

10354.17 N HCl Desmethylmianserin (Normianserin) 71936‐92‐0 14019.13 (±)‐Bupropion‐d9 hydrochloride (tert‐butyl‐d9) 1189725‐26‐5 Milnacipran Citalopram O 11889.15 N HCl Milnacipran hydrochloride 101152‐94‐7

9397.20 (±)‐Citalopram hydrobromide 59729‐32‐7 H2N Mirtazapine

N

N 9288.17 N Mirtazapine 85650‐52‐8

11330.19 (±)‐Desmethylcitalopram hydrochloride (Norcitalopram HCl) 97743‐99‐2

9455.17 Mirtazapine‐d3 (N‐methyl‐d3) 1216678‐68‐0

12043.16 Desmethylmirtazapine dihydrochloride (Normirtazepine 2HCl) 61337‐68‐6 (free base)

Moclobemide

10732.13 Moclobemide 71320‐77‐9

Nefazodone

11899.20 Nefazodone hydrochloride 82752‐99‐6

Opipramol 9403.16 Norfluoxetine‐d5 hydrochloride (propyl‐1,1,2,2,3‐d5) 1185132‐92‐6

Fluvoxamine

9403.16 Norfluoxetine‐d5 hydrochloride (propyl‐1,1,2,2,3‐d5) 1185132‐92‐6 10347.19 Fluvoxamine maleate 61718‐82‐9 Fluvoxamine

Imipramine 10347.19 Fluvoxamine maleate 61718‐82‐9

10853.19 Imipramine hydrochloride 113‐52‐0

Imipramine

Lofepramine 10853.19 Imipramine hydrochloride 113‐52‐0

11897.26 Lofepramine 23047‐25‐8 Lofepramine

Maprotiline 11897.26 Lofepramine 23047‐25‐8

11898.20 Maprotiline hydrochloride 10347‐81‐6

Maprotiline

Meprobamate

11898.20 Maprotiline hydrochloride 10347‐81‐6 9468.9 Meprobamate 57‐53‐4

Meprobamate

9233.9 Meprobamate‐d3 1185106‐66‐4 9468.9 Meprobamate 57‐53‐4

Mianserin

9233.9 Meprobamate‐d3 1185106‐66‐4 9413.18 Mianserin hydrochloride 21535‐47‐7

Mianserin

9413.18 Mianserin hydrochloride 21535‐47‐7 9414.18 Mianserin‐d3 hydrochloride (methyl‐d3) 1219804‐97‐3

10354.179414.18 MianserinDesmethylmianserin‐d3 hydrochloride (Normianserin) (methyl‐d3) 121980471936‐92‐97‐0‐3

Milnacipran

10354.17 Desmethylmianserin (Normianserin) 71936‐92‐0 11889.15 Milnacipran hydrochloride 101152‐94‐7

Milnacipran

Mirtazapine

11889.15 Milnacipran hydrochloride 101152‐94‐7 9288.17 Mirtazapine 85650‐52‐8 Chiron No. Structure Name CAS AgomelatineMirtazapine D D D N 9288.17 Mirtazapine 85650‐52‐8 9455.17 Mirtazapine‐d3 (N‐methyl‐d3) 1216678‐68‐0 11892.15 N Agomelatine 138112‐76‐2 N

NH 2HCl N 12043.169455.17 N DesmethylmirtazapineMirtazapine dihydrochloride‐d3 (N‐methyl (Normirtazepine‐d3) 2HCl) 613371216678‐68‐6 (free‐68‐ 0base) 14027.15 Agomelatine‐d3 (acetamide‐2,2,2‐d3) 1079389‐38‐0

Moclobemide O O 12043.16 N Desmethylmirtazapine dihydrochlorideAmitriptyline (Normirtazepine 2HCl) 61337‐68‐6 (free base) 10732.13 N Moclobemide 71320‐77‐9 H Cl MoclobemideNefazodone 2543.20 Amitriptyline hydrochloride 549‐18‐8 O

10732.13 N N N Moclobemide 71320‐77‐9 11899.20 O N N Cl Nefazodone hydrochloride 82752‐99‐6 HCl Nefazodone Opipramol Amitriptyline‐d3 hydrochloride (N‐methyl‐d3) 342611‐00‐1 10343.20 OH N 11899.20 N Nefazodone hydrochloride 82752‐99‐6 11641.23 Opipramol 315‐72‐0 N Opipramol

11852.20 Amitriptyline‐d6 hydrochlorideParoxetine (N,N‐dimethyl‐d6) 203645‐63‐0 F

O 9529.19 (‐)‐(3S,4R)‐Paroxetine hydrochloride hemihydrate 110429‐35‐1 2544.15 O O Dibenzosuberone (Amitriptyline Imp. A (EP)) 1210‐35‐1 HCl N H 0.5 H2O F

2697.20 Cyclobenzaprine hydrochloride (Amitriptyline Imp. B (EP)) 6202‐23‐9 O (‐)‐(3S,4R)‐Paroxetine‐d6 maleate (methylene‐d2, alpha‐N‐ 10367.19 D D 1435728‐64‐5 O HO O piperazine‐d4) O O D D N D H D OH Phenelzine 2698.19 D Nortriptyline hydrochloride (Amitriptyline Imp. C (EP)) 894‐71‐3 D D Phenelzine‐d5 sulfate (phenyl‐d5) (2‐Phenylethylhydrazine‐d5 12482.8 156‐51‐4 (unlabelled) NH sulfate) D N 2 H H SO D 2 4 Phenibut

9193.19 Nortriptyline‐d3 hydrochloride (N‐methyl‐d3) 203784‐52‐5 11395.10 O HCl Phenibut hydrochloride 3060‐41‐1 H N 2 OH Protriptyline

5‐(3‐Dimethylaminopropyl)‐10,11‐dihydro‐5H‐ 2711.20 1159‐03‐1 dibenzo[a,d]cyclohepten‐5‐ol (Amitriptyline Imp. D (EP)) 11902.19 HCl Protriptyline hydrochloride 1225‐55‐4

NH Amoxapine

Reboxetine O O 11992.17 Amoxapine 14028‐44‐5 HN O 14295.20 (+/‐) Reboxetine mesylate 98769‐84‐7

CH3SO3H Bupropion Sertraline 14181.13 Cl Bupropion hydrochloride (Amfebutamone HCl) 31677‐93‐7 Cl

HCl 9284.17 (+)‐(1S,4S)‐Sertraline hydrochloride 79559‐97‐0 14019.13 (±)‐Bupropion‐d9 hydrochloride (tert‐butyl‐d9) 1189725‐26‐5

HN Citalopram Cl Cl

HCl 12000.169397.20 rac(±)‐Norsertraline‐Citalopram hydrobromide hydrochloride 9179759729‐‐5732‐‐87

NH2

11330.19 (±)‐Desmethylcitalopram hydrochloride (Norcitalopram HCl) 97743‐99‐2 10601.17 (±)‐cis‐Sertraline‐d3 hydrochloride (N‐methyl‐d3) 1217741‐83‐7

10602.17 (±)‐trans‐Sertraline‐d3 hydrochloride (N‐methyl‐d3) 1330180‐66‐9

Tiagabine

13770.20 Tiagabine hydrochloride 145821‐59‐6

13769.20 Tiagabine‐methyl‐d6 hydrochloride 1217808‐68‐8

Tianeptine 11641.23 Opipramol 315‐72‐0

Paroxetine

9529.19 (‐)‐(3S,4R)‐Paroxetine hydrochloride hemihydrate 110429‐35‐1

(‐)‐(3S,4R)‐Paroxetine‐d6 maleate (methylene‐d2, alpha‐N‐ 10367.19 1435728‐64‐5 11641.23 piperazineOpipramol‐d4) 315‐72‐0

PhenelzineParoxetine

Phenelzine‐d5 sulfate (phenyl‐d5) (2‐Phenylethylhydrazine‐d5 12482.8 156‐51‐4 (unlabelled) sulfate) 9529.19 (‐)‐(3S,4R)‐Paroxetine hydrochloride hemihydrate 110429‐35‐1

Phenibut

11395.10 Phenibut hydrochloride 3060‐41‐1

(‐)‐(3S,4R)‐Paroxetine‐d6 maleate (methylene‐d2, alpha‐N‐ 10367.19 Protriptyline 1435728‐64‐5 piperazine‐d4)

11902.19 Protriptyline hydrochloride 1225‐55‐4 Phenelzine

Phenelzine‐d5 sulfate (phenyl‐d5) (2‐Phenylethylhydrazine‐d5 12482.8 156‐51‐4 (unlabelled) Reboxetinesulfate)

Phenibut 14295.20 (+/‐) Reboxetine mesylate 98769‐84‐7

11395.10 Phenibut hydrochloride 3060‐41‐1 Sertraline

Protriptyline

9284.17 (+)‐(1S,4S)‐Sertraline hydrochloride 79559‐97‐0 11902.19 Protriptyline hydrochloride 1225‐55‐4

Reboxetine

12000.1614295.20 rac(+/‐Norsertraline‐) Reboxetine hydrochloride mesylate 9179798769‐‐5784‐‐87

Chiron No. Structure Name CAS AgomelatineSertraline Cl Cl

HCl 11892.15 Agomelatine 138112‐76‐2 9284.17 (+)‐(1S,4S)‐Sertraline hydrochloride 79559‐97‐0 10601.17 (±)‐cis‐Sertraline‐d3 hydrochloride (N‐methyl‐d3) 1217741‐83‐7

HN D D D 14027.15 Cl Agomelatine‐d3 (acetamide‐2,2,2‐d3) 1079389‐38‐0 Cl

12000.16 HCl rac‐Norsertraline hydrochloride 91797‐57‐8

10602.17 (±)‐trans‐SertralineAmitriptyline‐d3 hydrochloride (N‐methyl‐d3) 1330180‐66‐9

HN D D 2543.20 D Amitriptyline hydrochloride 549‐18‐8 Tiagabine

10601.17 S (±)‐cis‐Sertraline‐d3 hydrochloride (N‐methyl‐d3) 1217741‐83‐7

13770.20 S N OH Tiagabine hydrochloride 145821‐59‐6 HCl 10343.20 O Amitriptyline‐d3 hydrochloride (N‐methyl‐d3) 342611‐00‐1 D S D D 13769.20 S N OH Tiagabine‐methyl‐d6 hydrochloride 1217808‐68‐8 HCl 10602.17 D O (±)‐trans‐Sertraline‐d3 hydrochloride (N‐methyl‐d3) 1330180‐66‐9 D D 11852.20 Amitriptyline‐d6 hydrochloride (N,N‐dimethyl‐d6) 203645‐63‐0 Tianeptine O O S N Cl Tiagabine

2544.15 HN Dibenzosuberone (Amitriptyline Imp. A (EP)) 1210‐35‐1 14128.2113770.20 TiagabineTianeptine hydrochloride 14582172797‐‐4159‐‐26

OH 2697.20 Cyclobenzaprine hydrochloride (Amitriptyline Imp. B (EP)) 6202‐23‐9 O 13769.20 Tiagabine‐methylTrazodone‐d6 hydrochloride 1217808‐68‐8 N N N O N 10862.19 HCl TrazodoneTianeptine hydrochloride 25332‐39‐2 2698.19 N Nortriptyline hydrochloride (Amitriptyline Imp. C (EP)) 894‐71‐3

Cl

D N D N D N D D O D N 12710.199193.19 HCl NortriptylineTrazodone‐d3d6 hydrochloride (N(propyl‐methyl‐d6)‐d3) 1181578203784‐‐5271‐‐51 N

Cl

Trimipramine 5‐(3‐Dimethylaminopropyl)‐10,11‐dihydro‐5H‐ 2711.20 1159‐03‐1 dibenzo[a,d]cyclohepten‐5‐ol (Amitriptyline Imp. D (EP)) N 9415.24 HO O Trimipramine maleate 521‐78‐8 O Amoxapine N OH

11992.17 Amoxapine 14028‐44‐5 N HO O 9416.24 O Trimipramine‐d3 maleate (N‐methyl‐d3) 1185245‐93‐5 D D OH Bupropion N D

14181.13 Bupropion hydrochlorideVenlafaxine (Amfebutamone HCl) 31677‐93‐7 O

14019.139417.17 HCl (±)‐BupropionVenlafaxine‐d9 hydrochloride hydrochloride (tert‐butyl‐d9) 118972599300‐78‐26‐4‐5 OH N

Citalopram O

HCl D 9418.17 D D Venlafaxine‐d6 hydrochloride (N,N‐dimethyl‐d6) 1062606‐12‐5 9397.20 OH (±)‐Citalopram hydrobromide 59729‐32‐7 N D D D

N 10335.16 O‐Desmethylvenlafaxine 93413‐62‐8

HO 11330.19 (±)‐Desmethylcitalopram hydrochloride (Norcitalopram HCl) 97743‐99‐2 HO Vortioxetine

11811.18 Vortioxetine hydrochloride 960203‐28‐5 14128.21 Tianeptine 72797‐41‐2

Trazodone

10862.19 Trazodone hydrochloride 25332‐39‐2

12710.19 Trazodone‐d6 hydrochloride (propyl‐d6) 1181578‐71‐1

Trimipramine

9415.24 Trimipramine maleate 521‐78‐8

9416.24 Trimipramine‐d3 maleate (N‐methyl‐d3) 1185245‐93‐5

5.5 An�depressant Mixes Venlafaxine Chiron oN . N ema CAS Concentra�on S-4886-ASS-ME An�depressant Mix 01: 13 components in 1 mL methanol 9530.19 Clomipramine hydrochloride 17321-77-6 500 µmol/L 10357.18 Norclomipramine hydrochloride 29854-14-6 500 µmol/L 9417.17 2543.20 Venlafaxine Amitriptyline hydrochloride hydrochloride 549-18-899300‐78‐ 2504 µmol/L 9413.18 Mianserin hydrochloride 21535-47-7 250 µmol/L 10354.17 Desmethylmianserin 71936-92-0 250 µmol/L 2698.19 Nortriptyline hydrochloride 894-71-3 250 µmol/L 9529.19 Paroxe�ne hydrochloride hemihydrate 110429-34-1 250 µmol/L 9397.20 Citalopram hydrobromide 59729-32-7 250 µmol/L 11330.19 Desmethylcitalopram hydrochloride 97743-99-2 250 µmol/L 9760.17 Fluoxe�ne 54910-89-3 500 µmol/L 9418.17 Venlafaxine9402.16 ‐d6 hydrochlorideNorfluoxe�ne (N,N hydrochloride‐dimethyl‐d6) 57226-68-31062606 ‐12 500‐5 µmol/L 9417.16 Venlafaxine hydrochloride 99300-78-4 625 µmol/L 10335.16 O-Desmethylvenlafaxine 93413-62-8 625 µmol/L (as free base)

S-4966-100-ME An�depressant Mix 02: 19 components in 1 mL methanol 10335.16 2543.20 O‐Desmethylvenlafaxine Amitriptyline hydrochloride 549-18-893413‐62‐8 9397.20 Citalopram hydrobromide 59729-32-7 Chiron No. Structure 11631.20 Name(S)-Citalopram oxalate 219861-08-2 CAS 9530.19 Clomipramine hydrochloride 17321-77-6 AgomelatineVortioxetine 11411.18 Desipramine hydrochloride 58-28-6 9400.19 Doxepin hydrochloride (cis+trans) 1229-29-4 (trans) 9291.17 Fluoxe�ne hydrochloride 56296-78-7 10347.19 Fluvoxamine maleate 61718-82-9 10853.19 Imipramine hydrochloride 113-52-0 11892.15 HCl Agomelatine 138112‐76‐2 11811.18 S 9413.18 Vortioxetine Mianserinhydrochloride hydrochloride 21535-47-7960203‐28100‐5 μg/mL 9288.17 Mirtazapine 85650-52-8 (as free base) N 10732.13 Moclobemide 71320-77-9 HN 10357.19 Norclomipramine hydrochloride 29854-14-6 2698.19 Nortriptyline hydrochloride 894-71-3 11641.23 Opipramol 315-72-0 (-)-(3S,4R)-Paroxe�ne hydrochloride 9529.19 110429-35-1 14027.15 Agomelatine‐d3 (acetamidehemih‐y2,2,2drate‐d3) 1079389‐38‐0 9284.17 (+)-(1S,4S)-Sertraline hydrochloride 79559-97-0 9415.24 Trimipramine maleate 521-78-8 9417.17 Venlafaxine hydrochloride 99300-78-4 Amitriptyline Antidepressant Mixes5.5 An�depressant Mixes Antipsychotic5.6 An�spycho�c and Antidepressant and An�depressant Mixes

Chiron oN . N ema CAS Concentra�on Chiron oN . N ema CAS Concentra�on S-4886-ASS-ME An�depressant Mix 01: 13 components in 1 mL methanol S-4983-ASS-ME An�psycho�c & An�depressant Mix 02: 6 components in 1 mL methanol 9530.192543.20 Clomipramine hydrochloride 17321-77-6 500 µmol/L Amitriptyline hydrochloride 549‐18‐8 10 µmol/L 11163.22 Fluphenazine dihydrochloride 146-56-5 10357.18 Norclomipramine hydrochloride 29854-14-6 500 µmol/L (4.38 µg/mL) 10 µmol/L 2543.20 Amitriptyline hydrochloride 549-18-8 250 µmol/L 10712.23 cis-(Z)-Flupen�xol dihydrochloride 51529-01-2 9413.18 Mianserin hydrochloride 21535-47-7 250 µmol/L (4.35 µg/mL) 10 µmol/L 10354.17 Desmethylmianserin 71936-92-0 250 µmol/L 9749.21 Perphenazine 58-39-9 2698.19 Nortriptyline hydrochloride 894-71-3 250 µmol/L (4.04 µg/mL) 20 µmol/L 9529.19 Paroxe�ne hydrochloride hemihydrate 110429-34-1 250 µmol/L 10284.22 Zuclopenthixol (cis+trans) 982-24-1 9397.20 Citalopram hydrobromide 59729-32-7 250 µmol/L (8.02 µg/mL) 10343.20 Amitriptyline‐d3 hydrochloride (N‐methyl‐d3) 342611‐00100‐1 µmol/L 11330.19 Desmethylcitalopram hydrochloride 97743-99-2 250 µmol/L 9284.17 (+)-(1S,4S)-Sertraline hydrochloride 79559-97-0 9760.17 Fluoxe�ne 54910-89-3 500 µmol/L (30.62 µg/mL) Norfluoxe�ne hydrochloride 57226-68-3 500 µmol/L 100 µmol/L 9402.16 12000.16 rac-Norsertraline hydrochloride 91797-57-8 9417.16 Venlafaxine hydrochloride 99300-78-4 625 µmol/L (29.22 µg/mL) 10335.16 O-Desmethylvenlafaxine 93413-62-8 625 µmol/L (as free base) (as free base) S-4932-25uM-ME An�psycho�c & An�depressant Mix 01: 7 components in 1 mL methanol 10345.21 Haloperidol 52-86-8 S-4966-100-ME11852.20 An�depressant Mix 02: 19 components in 1 mL methanol Amitriptyline3761.17 ‐d6 hydrochlorideOlanzapine (N,N‐dimethyl‐d6) 132539-06-1203645‐63‐0 2543.20 Amitriptyline hydrochloride 549-18-8 11913.16 N-Desmethylolanzapine 161696-76-0 25 μM 9397.20 Citalopram hydrobromide 59729-32-7 10337.23 Risperidone 106266-06-2 (as free base) 11631.20 (S)-Citalopram oxalate 219861-08-2 10338.23 (9RS)-9-Hydroxyrisperidone 144598-75-4 9530.19 Clomipramine hydrochloride 17321-77-6 9288.17 Mirtazapine [85650-52-8] 11411.18 Desipramine hydrochloride 58-28-6 11189.16 Desmethylmirtazapine hydrochloride 61337-68-6 (free base) 9400.19 Doxepin hydrochloride (cis+trans) 1229-29-4 (trans) 2544.15 Dibenzosuberone (Amitriptyline Imp. A (EP)) 1210‐35‐1 9291.17 Fluoxe�ne hydrochloride 56296-78-7 10347.19 Fluvoxamine maleate 61718-82-9 S-5204-25μM-ME An�psycho�c & An�depressant Mix 03: 8 components in 1 mL methanol 10853.19 Imipramine hydrochloride 113-52-0 10345.21 aH l epo r i od l 25 -86-8 9413.18 Mianserin hydrochloride 21535-47-7 100 μg/mL 3761.17 Olanzapine 132539-06-1 9288.17 Mirtazapine 85650-52-8 (as free base) 11913.16 N-Desmethylolanzapine 161696-76-0 25 μM 10732.132697.20 Moclobemide 71320-77-9 Cyclobenzaprine10337.23 hydrochloride (AmitriptylineRisperidone Imp. B (EP)) 106266-06-26202‐23‐9 10357.19 Norclomipramine hydrochloride 29854-14-6 10338.23 (9RS)-9-Hydroxyrisperidone 144598-75-4 (as free base) 2698.19 Nortriptyline hydrochloride 894-71-3 9288.17 Mirtazapine 85650-52-8 11641.23 Opipramol 315-72-0 12043.16 Desmethylmirtazapine dihydrochloride 61337-68-6 (freebase) (-)-(3S,4R)-Paroxe�ne hydrochloride 11811.18 Vor�oxe�ne hydrochloride 960203-28-5 9529.19 110429-35-1 hemihydrate 9284.17 (+)-(1S,4S)-Sertraline hydrochloride 79559-97-0 9415.24 Trimipramine maleate 521-78-8 S-4965-100-ME An�psycho�c Mix 01: 12 components in 1 mL methanol 9417.172698.19 Venlafaxine hydrochloride 99300-78-4 Nortriptyline10349.17 hydrochloride (Amitriptyline Amisulpride Imp. C (EP)) 71675-85-9 894‐71‐3 Biperiden Hydrochloride 10793.21 1235-82-1 5.6 An�spycho�c and An�depressant Mixes (Mixture of diastereomers) 10350.17 Chlorpromazine hydrochloride 69-09-0 Chiron oN . N ema CAS Concentra�on 9275.18 Clozapine 5786-21-0 S-4983-ASS-ME An�psycho�c & An�depressant Mix 02: 6 components in 1 mL methanol 10345.21 Haloperidol 52-86-8 100 μg/mL 10 µmol/L 10338.23 9-Hydroxyrisperidone 144598-75-4 (as free base) 11163.22 Fluphenazine dihydrochloride 146-56-5 (4.38 µg/mL) 11913.16 N-Demethylolanzapine 161696-76-0 9193.19 10 µmol/L 10807.17Nortriptyline‐d3Norclozapine hydrochloride (N-Desmethyl (N‐methyl Clozapine)‐d3) 6104-71-8203784‐52‐5 10712.23 cis-(Z)-Flupen�xol dihydrochloride 51529-01-2 (4.35 µg/mL) 3761.17 Olanzapine 132539-06-1 10 µmol/L 10835.46 Que�apine hemifumarate 111974-72-2 9749.21 Perphenazine 58-39-9 (4.04 µg/mL) 10337.23 Risperidone 106266-06-2 20 µmol/L 11419.21 Thioridazine hydrochloride 130-61-0 10284.22 Zuclopenthixol (cis+trans) 982-24-1 (8.02 µg/mL) 100 µmol/L 9284.17 (+)-(1S,4S)-Sertraline hydrochloride 79559-97-0 (30.62 µg/mL) 5‐(3‐Dimethylaminopropyl)‐10,11‐dihydro‐5H‐ 2711.20 1159‐03‐1 100 µmol/L dibenzo[a,d]cyclohepten‐5‐ol (Amitriptyline Imp. D (EP)) 12000.16 rac-Norsertraline hydrochloride 91797-57-8 (29.22 µg/mL) (as free base) For ordering and information about prices and delivery in your country, pleaseAmoxapine contact your local distributor: S-4932-25uM-ME An�psycho�c & An�depressant Mix 01: 7 components in 1 mL methanol 10345.21 Haloperidol 52-86-8 3761.17 Olanzapine 132539-06-1 11913.16 N-Desmethylolanzapine 161696-76-0 Amoxapine 14028‐44‐5 11992.17 25 μM 10337.23 Risperidone 106266-06-2 (as free base) 10338.23 (9RS)-9-Hydroxyrisperidone 144598-75-4 9288.17 Mirtazapine [85650-52-8] 11189.16 Desmethylmirtazapine hydrochloride 61337-68-6 (free base) Bupropion

S-5204-2514181.13μM-ME An�psycho�c & An�depressant Mix 03: 8 components in 1 mL methanol Bupropion hydrochloride (Amfebutamone HCl) 31677‐93‐7 10345.21 aH l epo r i od l 25 -86-8 3761.17 Olanzapine 132539-06-1 11913.16 N-Desmethylolanzapine 161696-76-0 10337.23 Risperidone 106266-06-2 25 μM 10338.2314019.13 (9RS)-9-Hydroxyrisperidone 144598-75-4 (as free base) (±)‐Bupropion‐d9 hydrochloride (tert‐butyl‐d9) 1189725‐26‐5 9288.17 Mirtazapine 85650-52-8 12043.16 Desmethylmirtazapine dihydrochloride 61337-68-6 (freebase) 11811.18 Vor�oxe�ne hydrochloride 960203-28-5 Citalopram

S-4965-100-ME An�psycho�c Mix 01: 12 components in 1 mL methanol 10349.17 Amisulpride 71675-85-9 Biperiden Hydrochloride 10793.219397.20 1235-82-1 (±)‐Citalopram hydrobromide 59729‐32‐7 (Mixture of diastereomers) 10350.17 Chlorpromazine hydrochloride 69-09-0 9275.18 Clozapine 5786-21-0 10345.21 Your quality Haloperidol is our business52-86-8 100 μg/mL 10338.23 9-Hydroxyrisperidone 144598-75-4 (as free base) 11913.16 N-Demethylolanzapine 161696-76-0 10807.17 Norclozapine (N-Desmethyl Clozapine) 6104-71-8 3761.1711330.19 Chiron OlanzapineAS | Stiklestadveien 132539-06-1 1 | N-7041 | Trondheim(±)‐Desmethylcitalopram | Norway hydrochloride (Norcitalopram HCl) 97743‐99‐2 10835.46 Que�apine hemifumarate 111974-72-2 10337.23 Risperidone 106266-06-2 11419.21 Thioridazine +47 73 hydrochloride 87 44 90 | Fax.:130-61-0 +47 73 87 44 99 [email protected] www.chiron.no BMF 84 | v1 | 10/20