3,4-Methylenedioxy- -Pyrrolidinohexanophenone

3,4-Methylenedioxy--Pyrrolidinohexanophenone The Drug Enforcement Administration's Special Testing and Research Laboratory generated this monograph using structurally confirmed reference material.

O N O

3CH

1. GENERAL INFORMATION

IUPAC Name: 1-(1,3-benzodioxol-5-yl)-2-(pyrrolidin-1-yl)hexan-1-one

CAS#: 24622-61-5

Synonyms: 3,4-MD--PHP; 3,4-MDPHP; 3,4-Methylenedioxy--PHP

Source: DEA Reference Material Collection

Appearance: Tan powder

UVmax(nm): Not determined

2. CHEMICAL AND PHYSICAL DATA

2.1 CHEMICAL DATA

Form Chemical Formula Molecular Weight Melting Point (oC)

Base C17H23NO3 289.37 Not Determined

HCl C17H23NO3 HCl 325.83 Not Determined

Latest Revision: 9/4/2019 SWGDRUG.org/monographs.htm Page 1 of 5 3,4-Methylenedioxy--Pyrrolidinohexanophenone The Drug Enforcement Administration's Special Testing and Research Laboratory generated this monograph using structurally confirmed reference material.

3. QUALITATIVE DATA

3.1 NUCLEAR MAGNETIC RESONANCE

Sample Preparation: Dilute analyte to ~17 mg/mL in methanol-d4 containing TMS for 0 ppm reference and

1,4-BTMSB-d4 as quantitative internal standard.

Instrument: 400 MHz NMR spectrometer Parameters: Spectral width: at least containing -3 ppm through 13 ppm Pulse angle: 90o Delay between pulses: 45 seconds

1 HNMR: 3,4-Methylenedioxy--Pyrrolidinohexanophenone HCl; Lot# 0464802-38; methanol-d4; 400MHz

BTMSB

methanol-d4

TMS

111 2 1 112 6 34

8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0

CD3OD

1 1 1 2 1 2 1 1 6 4 3

7.76 7.52 7.025 6.13 5.250 3.70 3.65 3.60 3.350 3.050 2.2 2.1 2.0 1.3 1.2 1.1 0.850 Latest Revision: 9/4/2019 SWGDRUG.org/monographs.htm Page 2 of 5 3,4-Methylenedioxy--Pyrrolidinohexanophenone The Drug Enforcement Administration's Special Testing and Research Laboratory generated this monograph using structurally confirmed reference material.

3.2 GAS CHROMATOGRAPHY/MASS SPECTROMETRY

Sample Preparation: Dilute analyte ~4.7 mg/mL in MeOH

Instrument: Agilent gas chromatograph operated in split mode with MS detector Column: HP-5 MS (or equivalent); 30m x 0.25 mm x 0.25 m Carrier Gas: Helium at 1.5 mL/min Temperatures: Injector: 280oC MSD transfer line: 280oC MS Source: 230oC MS Quad: 150oC Oven program: 1) 100oC initial temperature for 1.0 min 2) Ramp to 280oC at 12 oC/min 3) Hold final temperature for 9.0 min Injection Parameters: Split Ratio = 25:1, 1 L injected MS Parameters: Mass scan range: 30-550 amu Threshold: 250 Tune file: stune.u Acquisition mode: scan Retention Time: 13.21 min

EI Mass Spectrum: 3,4-Methylenedioxy--Pyrrolidinohexanophenone HCl; Lot# 0464802-38

] 140140

6 140 [x 10 [x Intensity

141141 2 4242 6969 9797 6565 110110 4141 55 8484 9696 121121 149 232232 288288

40 60 80 100 120 140 160 180 200 220 240 260 280 m/z

] 140140 141141 5 121121 140140 141141 6565 8484 9696 [x 10 [x

6969 9797 Intensity 4242 4141 5555 3 110110 6363 110110 9898 138138 2 5454 7070 3939 4343 39 174174 175175 232232 289289 1 5353 232232 289 3030 164164 177177 288288 4444 164 177177 203203 204204 230230 260260 288288 160160 190190 202202 214214 233233 258258 287287

40 60 80 100 120 140 160 180 200 220 240 260 280 m/z Latest Revision: 9/4/2019 SWGDRUG.org/monographs.htm Page 3 of 5 3,4-Methylenedioxy--Pyrrolidinohexanophenone The Drug Enforcement Administration's Special Testing and Research Laboratory generated this monograph using structurally confirmed reference material.

3.3 INFRARED SPECTROSCOPY (FTIR)

Instrument: FTIR with diamond ATR attachment (1 bounce) Scan Parameters: Number of scans: 32 Number of background scans: 32 Resolution: 4 cm-1 Sample gain: 1 Aperture: 150

FTIR ATR (Diamond 1 Bounce): 3,4-Methylenedioxy--Pyrrolidinohexanophenone HCl; Lot# 0464802-38 309330933093 3093 3093 3093 3093 3093 3093 3093 3093 3093 3093 3093 3093 30933093 3093 3093 3093 3093 3093 280428042804 2804 2804 2804 2804 2804 2804 2804 2804 2804 2804 2804 2804 28042804 2804 2804 2804 2804 2804 286928692869 2869 2869 2869 2869 2869 2869 2869 2869 2869 2869 2869 2869 28692869 2869 2869 2869 2869 2869 252525252525247624762476 2525 2525 2525 2476 2476 2476 2525 2525 2525 2476 2476 2476 2525 2525 2525 2476 2476 2476 2525 2525 2525 2476 2476 2476 2525252524762476 2525 2525 2476 2476 2525 2525 2476 2476 2525 2476 %Transmittance 259925992599 2599 2599 2599 2599 2599 2599 2599 2599 2599 2599 2599 2599 25992599 2599 2599 2599 2599 2599 295029502950 2950 2950 2950 2950 2950 2950 2950 2950 2950256925692569 2950 2950 2950 2569 2569 2569 2569 2569 2569 2569 2569 2569 2569 2569 2569 29502950 2950 2950 2950 2950 25692569 2569 2569 2569 2569 2950 2569 291429142914 2914 2914 2914 2914 2914 2914 2914 2914 2914 2914 2914 2914 29142914 2914 2914 2914 2914 2914 429429429 429 429 429 429 429 429 429 429 429 429 429 429 429429429429429429 72 429 160816081608 1608 1608 1608 1608 1608 1608 1608 1608 1608 1608 1608 1608 16081608 1608 1608 1608 1608 1608 739739739 739 739 739 739 739 739 739 739 739 739 739 739 739739739739739739 739 64 805805805 805 805 805 805 805 805 805 805 805 805 805 805 805805805805805805 805 568568568 568 568 568 568 568 568 568 568 568 568 568 568 568568568568568568 568 149014901490 1490 1490 1490 1490 1490 1490 1490 1490 1490 1490 1490 1490 14901490 1490 1490 1490 1490 56 1490 168316831683 1683 1683 1683 1683 1683 1683 1683 1683 1683 1683 1683 1683 16831683 1683 1683 1683 1683 1683 135613561356 1356 1356 1356 1356 1356 1356 1356 1356 1356 1356 1356 1356 13561356 1356 1356 1356 1356 1356 143614361436 1436 1436 1436 1436 1436 1436 1436 1436 1436 1436 1436 1436 14361436 1436 1436 1436 1436 1436 110511051105 1105 1105 1105 1105 1105 1105 1105 1105 1105 1105 1105 1105 11051105 1105 1105 1105 1105 1105 928928928 928 928 928 928 928 928 928 928 928 928 928 928 928928928928928928 48 928

40 103210321032 1032 1032 1032 1032 1032 1032 1032 1032 1032 1032 1032 1032 10321032 1032 1032 1032 1032 32 1032 125212521252 1252 1252 1252 1252 1252 1252 1252 1252 1252 1252 1252 1252 12521252 1252 1252 1252 1252 24 1252

3500 3000 2500 2000 1500 1000 Wavenumber (cm-1) 671671671 671 671 671 671 671 671 671 671 671 671 671 671 671671671671671671 671 515515515 515 515 515 515 515 515 515 515 515 515 515 515 515515515515515515 515 113811381138 1138 1138 1138 1138 1138 1138 1138 1138 1138 1138 1138 1138 11381138 1138 1138 1138 1138 1138 628628628 628 628 628 628 628 628 628 628 628 628 628 628 412412412 412 412 412 412 412 412 412 412 412 412 412 412 628628628628628628 412412412412412412 628 412 %Transmittance 130213021302 1302 1302 1302 1302 1302 1302 1302 1302 1302 1302 1302 1302 13021302 1302 1302 1302 1302 1302 727727727 727 727 727 727 727 727 727 727 727 727 727 727 727727727727727727715715715 715 715 715 715 715 715 715 715 715 715 715 715 727 715715715715715715 715 478478478 478 478 478 478 478 478 478 478 478 478 478 478 954954954 954 954 954 954 954 954 954 954 954 954 954 954 478478478478478478 954954954954954954 478 954 141414141414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 14141414 1414 1414 1414 1414 1414 429429429 429 429 429 429 429 429 429 429 429 429 429 429 429429429429429429 108210821082 1082 1082 1082 1082 1082 1082 1082 1082 1082 1082 1082 1082 429 10821082 1082 1082 1082 1082 1082 166216621662 1662 1662 1662 1662 1662 1662 1662 1662 1662 1662 1662 1662 16621662 1662 1662 1662 1662 889889889 889 889 889 889 889 889 889 889 889 889 889 889 1662 889889889889889889 889 862862862 862 862 862 862 862 862 862 862 862 862 862 862 147114711471 1471 1471 1471 1471 1471 1471 1471 1471 1471 1471 1471 1471 862862862862862862 14711471 1471 1471 1471 1471 862 72 1471 138313831383 1383 1383 1383 1383 1383 1383 1383 1383 1383 1383 1383 1383 13831383 1383 1383 1383 1383 1383 160816081608 1608 1608 1608 1608 1608 1608 1608 1608 1608 1608 1608 1608 16081608 1608 1608 1608 1608 1608 121512151215 1215 1215 1215 1215 1215 1215 1215 1215 1215 1215 1215 1215 12151215 1215 1215 1215 1215 1215 739739739 739 739 739 739 739 739 739 739 739 739 739 739 739739739739739739 739 836836836 836 836 836 836 836 836 836 836 836 836 836 836 836836836836836836 836 134013401340 1340 1340 1340 1340 1340 1340 1340 1340 1340 1340 1340 1340 13401340 1340 1340 1340 1340 578578578 578 578 578 578 578 578 578 578 578 578 578 578 1340 578578578578578578 578 992992992 992 992 992 992 992 992 992 992 992 992 992 992 992992992992992992 992 150415041504 1504 1504 1504 1504 1504 1504 1504 1504 1504 1504 1504 1504 15041504 1504 1504 1504 1504 1504 127712771277 1277 1277 1277 1277 1277 1277 1277 1277 1277 1277 1277 1277 12771277 1277 1277 1277 1277 64 1277 872872872 872 872 872 872 872 872 872 872 872 872 872 872 872872872872872872 872 805805805 805 805 805 805 805 805 805 805 805 805 805 805 805805805805805805 805 568568568 568 568 568 568 568 568 568 568 568 568 568 568 568568568568568568 568 149014901490 1490 1490 1490 1490 1490 1490 1490 1490 1490 1490 1490 1490 14901490 1490 1490 1490 1490 56 1490 168316831683 1683 1683 1683 1683 1683 1683 1683 1683 1683 1683 1683 1683 16831683 1683 1683 1683 1683 1683 135613561356 1356 1356 1356 1356 1356 1356 1356 1356 1356 1356 1356 1356 13561356 1356 1356 1356 1356 1356 143614361436 1436 1436 1436 1436 1436 1436 1436 1436 1436 1436 1436 1436 14361436 1436 1436 1436 1436 1436 110511051105 1105 1105 1105 1105 1105 1105 1105 1105 1105 1105 1105 1105 11051105 1105 1105 1105 1105 1105 928928928 928 928 928 928 928 928 928 928 928 928 928 928 928928928928928928 48 928

1900 1800 1700 1600 1500 1400 1300 1200 1100 1000 900 800 700 Wavenumber (cm-1) Latest Revision: 9/4/2019 SWGDRUG.org/monographs.htm Page 4 of 5 3,4-Methylenedioxy--Pyrrolidinohexanophenone The Drug Enforcement Administration's Special Testing and Research Laboratory generated this monograph using structurally confirmed reference material.

4. ADDITIONAL RESOURCES

Kaizaki-Mitsumoto, A.; Noguchi, N.; Yamaguchi, S.; et. al. Three 25-NBOMe-type drugs, three other phenethylamine-type drugs (25I-NBMD, RH34, and escaline), eight cathinone derivatives, and a phencyclidine analog MMXE, newly identified in ingredients of drug products before they were sold on the drug market. Forensic Toxicology. DOI 10.1007/s11419-015-0293-6.

Latest Revision: 9/4/2019 SWGDRUG.org/monographs.htm Page 5 of 5