5-Methoxy-DALT The Drug Enforcement Administration's Special Testing and Research Laboratory generated this monograph using structurally confirmed reference material.

H2C

N CH2

O H3C

N H

1. GENERAL INFORMATION

IUPAC Name: N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-(prop-2-en-1-yl)prop-2-en-1-amine

CAS#: 928822-98-4 (Base)

Synonyms: 5-MeO-DALT, 5-Methoxy-N,N-Diallyltryptamine, N,N-Diallyl-5-methoxytryptamine

Source: DEA Reference Material Collection

Appearance: White powder (Base and HCl)

UVmax(nm): 220 (Base)

2. CHEMICAL AND PHYSICAL DATA

2.1 CHEMICAL DATA

Form Molecular Weight Melting Point (oC)

Base C17H22N2O 270 105.1 . HCl C17H22N2O HCl 306 160.3

Latest Revision: 07/30/15 SWGDRUG.org/monographs.htm Page 1 of 7 5-Methoxy-DALT 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: (Base) - Dilute analyte to ~10 mg/mL in CDCl3 containing TMS for 0 ppm reference and methenamine 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, 5-Methoxy-DALT Base, Lot K8H81105, CDCl3, 400MHz Methenamine

10

9

8

7

6

5

4

3 TMS 2 CHCl3

1 HDO

0 1 1 1 1 2 4 3 4 4

8 7 6 5 4 3 2 1 0

CHCl3

1 1 1 1 1 2 4 3 4 4

8.0 7.9 7.25 7.00 6.00 5.90 5.25 5.15 3.90 3.80 3.25 3.20 2.90 2.80 Latest Revision: 07/30/15 SWGDRUG.org/monographs.htm Page 2 of 7 5-Methoxy-DALT The Drug Enforcement Administration's Special Testing and Research Laboratory generated this monograph using structurally confirmed reference material.

Sample Preparation: (HCl) Dilute analyte to ~30 mg/mL in D2O containing TSP for 0 ppm reference and maleic acid as quantitative internal standard.

1 HNMR, 5-Methoxy-DALT HCl, Lot RM-131001-04, D2O, 400MHz

HDO

10

9

8

7

6

5 Maleic Acid (ISTD)

4

3 TSP 2

1

0 1 1 1 1 2 4 34 2 2

8 7 6 5 4 3 2 1 0

1 1 1 1 2 4 3 4 2 2

7.25 7.00 5.90 5.85 5.625 5.575 3.90 3.85 3.80 3.4 3.3 3.2

Latest Revision: 07/30/15 SWGDRUG.org/monographs.htm Page 3 of 7 5-Methoxy-DALT 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 mg/mL into (Base).

Instrument: Agilent gas chromatograph operated in split mode with MS detector Column: DB-1 MS (or equivalent); 30m x 0.25 mm x 0.25 mm Carrier Gas: Helium at 1 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 300oC at 12 oC/min 3) Hold final temperature for 9.0 min Injection Parameters: Split Ratio = 20:1, 1 mL injected MS Parameters: Mass scan range: 30-550 amu Threshold: 100 Tune file: stune.u Acquisition mode: scan Retention Time: 14.548 min EI Mass Spectrum, 5-Methoxy-DALT Base, Lot K8H81105 ] 6 110 110 110 110 110 110 110 110 110 110 110 110 110 110 110 110 110 110 110 110 110 [x 10 Intensity

0.50 41 41 41 41 41 41 41 41 41 41 41 41 41 41 41 41 41 41 0.25 41 41 41 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 160 117 117 117 145 145 145 117 117 117 117 117 145 145 145 145 145 117 117 117 117 117 145 145 145 145 145 117 117 117 117 117 145 145 145 145 145 117 117 117 145 145 145 68 68 68 68 68 68 68 68 68 68 68 68 68 130 130 130 68 68 68 68 68 81 81 81 130 130 130 130 130 68 68 68 81 81 81 81 81 130 130 130 130 130 81 81 81 81 81 130 130 130 130 130 81 81 81 81 81 130 130 130 81 81 81 174 174 174 55 55 55 174 174 174 174 174 55 55 55 55 55 174 174 174 174 174 55 55 55 55 55 174 174 174 174 174 55 55 55 55 55 174 174 174 55 55 55 270 270 270 270 270 270 270 270 241 241 241 270 270 270 270 270 229 229 229 241 241 241 241 241 270 270 270 270 270 229 229 229 229 229 241 241 241 241 241 270 270 270 186 186 186 199 199 199 229 229 229 229 229 241 241 241 241 241 186 186 186 186 186 199 199 199 199 199 229 229 229 229 229 241 241 241 186 186 186 186 186 199 199 199 199 199 229 229 229 186 186 186 186 186 199 199 199 199 199 EI+ 186 186 186 199 199 199

40 60 80 100 120 140 160 180 200 220 240 260 m/z ] 4 41 41 41 55 55 55 68 68 68 81 81 81 110 110 110 117 117 117 130 130 130 145 145 145 160 160 160 174 174 174 41 41 41 41 41 55 55 55 55 55 68 68 68 68 68 81 81 81 81 81 110 110 110 110 110 117 117 117 117 117 130 130 130 130 130 145 145 145 145 145 160 160 160 160 160 174 174 174 174 174 41 41 41 41 41 55 55 55 55 55 68 68 68 68 68 81 81 81 81 81 110 110 110 110 110 117 117 117 117 117 130 130 130 130 130 145 145 145 145 145 160 160 160 160 160 174 174 174 174 174 41 41 41 41 41 55 55 55 55 55 68 68 68 68 68 81 81 81 81 81 110 110 110 110 110 117 117 117 117 117 130 130 130 130 130 145 145 145 145 145 160 160 160 160 160 174 174 174 174 174 41 41 41 55 55 55 68 68 68 81 81 81 110 110 110 117 117 117 130 130 130 145 145 145 160 160 160 174 174 174 270 270 270 270 270 270 270 270 270 270 270 270 270 270 270 270 270 270 270 270 270 [x 10 241 241 241 241 241 241 241 241 241 241 241 241 241 241 241 241 241 241 241 241 241 229 229 229 229 229 229 229 229 229 229 229 229 229 229 229 229 229 229 229 229 229 199 199 199 199 199 199 199 199 199 199 199 199 199 199 199 199 199 199 199 199 199 186 186 186 186 186 186 186 186 186 186 186 186 186 186 186 186 186 186 186 186 186 EI+ Intens... 40 60 80 100 120 140 160 180 200 220 240 260 m/z Latest Revision: 07/30/15 SWGDRUG.org/monographs.htm Page 4 of 7 5-Methoxy-DALT The Drug Enforcement Administration's Special Testing and Research Laboratory generated this monograph using structurally confirmed reference material.

3.3 INFRARED SPECTROSCOPY (FTIR)

Insrument: FTIR with diamond ATR attachment (3 bounce) Scan Parameters: Number of scans: 32 Number of background scans: 32 Resolution: 4 cm-1 Sample gain: 8 Aperture: 150 FTIR, ATR (Diamond, 3 Bounce), 5-Methoxy-DALT Base (Lot K8H81105) 2877 2877 2877 2877 2877 2877 2877 2877 2877 2877 2877 2877 2877 2877 2877 2877 2877 2877 2877 2877 2877 2839 2839 2839 2839 2839 2839 2839 2839 2839 2839 2839 2839 2839 2839 2839 2839 2839 2839 2839 2839 2839 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1173 1173 1173 1173 1173 1173 1173 1173 1173 1173 1173 1173 1173 1585 1585 1585 1173 1173 1173 1173 1173 1585 1585 1585 1585 1585 1173 1173 1173 1585 1585 1585 1585 1585 1585 1585 1585 1585 1585 1585 1585 1585 %Transmittance 1240 1240 1240 1240 1240 1240 1240 1240 1240 1240 1240 1240 1240 1240 1240 1240 1240 1240 1491 1491 1491 1240 1240 1240 1491 1491 1491 1491 1491 1491 1491 1491 1491 1491 1491 1491 1491 1491 1491 528 528 528 1491 1491 1491 528 528 528 528 528 528 528 528 528 528 528 528 528 528 528 528 528 528 1059 1059 1059 1059 1059 1059 1059 1059 1059 1059 1059 1059 1059 1059 1059 1059 1059 1059 1007 1007 1007 1448 1448 1448 1059 1059 1059 1007 1007 1007 1007 1007 1448 1448 1448 1448 1448 1007 1007 1007 1007 1007 1448 1448 1448 1448 1448 1007 1007 1007 1007 1007 1448 1448 1448 1448 1448 1007 1007 1007 80 1448 1448 1448 839 839 839 839 839 839 839 839 839 839 839 839 839 839 839 839 839 839 839 839 839 426 426 426 426 426 426 426 426 426 426 426 426 426 426 426 426 426 426 426 426 426 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 1105 1105 1105 760 760 760 1105 1105 1105 1105 1105 760 760 760 760 760

75 1105 1105 1105 1105 1105 760 760 760 760 760 1105 1105 1105 1105 1105 760 760 760 760 760 1105 1105 1105 760 760 760 1219 1219 1219 1219 1219 1219 1219 1219 916 916 916 1219 1219 1219 1219 1219 916 916 916 916 916 407 407 407 1219 1219 1219 1219 1219 916 916 916 916 916 407 407 407 407 407 1219 1219 1219 916 916 916 916 916 407 407 407 407 407 916 916 916 407 407 407 407 407 407 407 407 638 638 638 638 638 638 638 638 638 638 638 638 638 638 638 638 638 638 638 638 638 70 791 791 791 791 791 791 791 791 791 791 791 791 791 791 791 791 791 791 791 791 791 65

60

55

3500 3000 2500 2000 1500 Wavenumber (cm-1) 1273 1273 1273 1273 1273 1273 1273 1273 1273 1273 1273 1273 1273 1273 1273 1273 1273 1273 1273 1273 1273 1352 1352 1352 1352 1352 1352 1352 1352 1352 1352 1352 1352 1352 1352 1352 1352 1352 1352 1352 1352 1352 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1414 1173 1173 1173 1173 1173 1173 1173 1173 1173 1173 1173 1173 1173 1585 1585 1585 1173 1173 1173 1173 1173 1585 1585 1585 1585 1585 1173 1173 1173 1585 1585 1585 1585 1585 1585 1585 1585 1585 1585 1585 1585 1585 %Transmittance 978 978 978 978 978 978 978 978 978 978 978 978 978 978 978 978 978 978 978 978 978 1240 1240 1240 1240 1240 1240 1240 1240 1240 1240 1240 1240 1240 1491 1491 1491 1240 1240 1240 1240 1240 1491 1491 1491 1491 1491 1240 1240 1240 1491 1491 1491 1491 1491 1491 1491 1491 1491 1491 1491 1491 1491 1059 1059 1059 1059 1059 1059 1059 1059 1059 1059 1059 1059 1059 1007 1007 1007 1059 1059 1059 1059 1059 1007 1007 1007 1007 1007 1448 1448 1448 1059 1059 1059 1007 1007 1007 1007 1007 1448 1448 1448 1448 1448 1007 1007 1007 1007 1007 1448 1448 1448 1448 1448 1007 1007 1007 1448 1448 1448 1448 1448 1448 1448 1448 852 852 852 852 852 852 852 852 499 499 499 852 852 852 852 852 499 499 499 499 499 852 852 852 852 852 499 499 499 499 499 852 852 852 499 499 499 499 499 499 499 499 579 579 579 579 579 579 579 579 579 579 579 579 579 579 579 579 579 579 80 579 579 579 488 488 488 488 488 488 488 488 488 488 488 488 488 488 488 488 488 488 488 488 488 802 802 802 802 802 802 802 802 802 802 802 802 802 802 802 802 802 802 802 802 802 714 714 714 714 714 714 714 714 714 714 714 714 714 714 714 714 714 714 714 714 714 839 839 839 839 839 839 839 839 442 442 442 839 839 839 839 839 442 442 442 442 442 839 839 839 839 839 442 442 442 442 442 839 839 839 442 442 442 442 442 442 442 442 426 426 426 426 426 426 426 426 426 426 426 426 426 426 426 426 426 426 426 426 426 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 1211 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 1105 1105 1105 760 760 760

75 1105 1105 1105 1105 1105 760 760 760 760 760 1105 1105 1105 1105 1105 760 760 760 760 760 1105 1105 1105 1105 1105 760 760 760 760 760 1105 1105 1105 760 760 760 1219 1219 1219 1219 1219 1219 1219 1219 916 916 916 407 407 407 1219 1219 1219 1219 1219 916 916 916 916 916 407 407 407 407 407 1219 1219 1219 1219 1219 916 916 916 916 916 407 407 407 407 407 1219 1219 1219 916 916 916 916 916 407 407 407 407 407 916 916 916 407 407 407 638 638 638 638 638 638 638 638 638 638 638 638 638 638 638 638 638 638 638 638 638 70 791 791 791 791 791 791 791 791 791 791 791 791 791 791 791 791 791 791 791 791 791 65

60

55

1700 1600 1500 1400 1300 1200 1100 1000 900 800 700 Wavenumber (cm-1) Latest Revision: 07/30/15 SWGDRUG.org/monographs.htm Page 5 of 7 5-Methoxy-DALT The Drug Enforcement Administration's Special Testing and Research Laboratory generated this monograph using structurally confirmed reference material.

FTIR, ATR (Diamond, 3 Bounce), 5-Methoxy-DALT HCl, Lot RM-131001-04 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 903 903 903 903 903 903 903 903 903 903 903 903 903 903 903 903 903 903 903 903 903 575 575 575 575 575 575 575 575 575 575 575 575 575 575 575 575 575 575 575 575 575 %Transmittance 2528 2528 2528 2528 2528 2528 2528 2528 2528 2528 2528 2528 2528 2528 2528 2528 2528 2528 2528 2528 2528 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 2469 2469 2469 2469 2469 2469 2469 2469 2469 2469 2469 2469 2469 2469 2469 2469 2469 2469 2469 2469 2469 729 729 729 729 729 729 729 729 729 729 729 729 729 729 729 729 729 729 729 729 729 2505 2505 2505 2505 2505 2505 2505 2505 2505 2505 2505 2505 2505 2505 2505 2505 2505 2505 2505 2505 2505 991 991 991 991 991 991 991 991 1462 1462 1462 991 991 991 991 991 1462 1462 1462 1462 1462 991 991 991 991 991 1462 1462 1462 1462 1462 991 991 991 1462 1462 1462 1462 1462 1462 1462 1462 3165 3165 3165 3165 3165 3165 3165 3165 3165 3165 3165 3165 3165 3165 3165 3165 3165 3165 3165 3165 3165 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 72 1240 1240 1240 714 714 714 1240 1240 1240 1240 1240 714 714 714 714 714 1240 1240 1240 1240 1240 714 714 714 714 714 1240 1240 1240 1240 1240 714 714 714 714 714 1240 1240 1240 714 714 714 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 831 831 831 831 831 831 831 831 831 831 831 831 831 831 831 831 831 831 831 831 831 642 642 642 642 642 642 642 642 642 642 642 642 642 642 642 642 642 642 1493 1493 1493 642 642 642 1493 1493 1493 1493 1493 1493 1493 1493 1493 1493 1493 1493 1493 1493 1493 64 1493 1493 1493 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 804 804 804 804 804 804 804 804 804 804 804 804 804 804 804 804 804 804 804 804 804 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 56 933 933 933

48

3500 3000 2500 2000 1500 Wavenumber (cm-1) 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1587 1039 1039 1039 1039 1039 1039 1039 1039 1039 1039 1039 1039 1039 903 903 903 1039 1039 1039 1039 1039 903 903 903 903 903 1039 1039 1039 903 903 903 903 903 903 903 903 903 903 903 903 903 1296 1296 1296 1296 1296 1296 1296 1296 1296 1296 1296 1296 1296 1296 1296 1296 1296 1296 1296 1296 1296 575 575 575 575 575 575 575 575 575 575 575 575 575 575 575 575 575 575 575 575 575 %Transmittance 760 760 760 760 760 760 760 760 760 760 760 760 760 760 760 760 760 760 760 760 760 1001 1001 1001 1001 1001 1001 1001 1001 1001 1001 1001 1001 1001 1001 1001 1001 1001 1001 1001 1001 1001 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 1423 656 656 656 656 656 656 656 656 656 656 656 656 656 656 656 656 656 656 656 656 656 1066 1066 1066 1066 1066 1066 1066 1066 1066 1066 1066 1066 1066 1066 1066 1066 1066 1066 729 729 729 1066 1066 1066 729 729 729 729 729 729 729 729 729 729 729 729 729 729 729 729 729 729 991 991 991 1462 1462 1462 991 991 991 991 991 1462 1462 1462 1462 1462 991 991 991 991 991 1462 1462 1462 1462 1462 991 991 991 991 991 1462 1462 1462 1462 1462 991 991 991 1462 1462 1462 1186 1186 1186 1186 1186 1186 1186 1186 1186 1186 1186 1186 1186 1186 1186 1186 1186 1186 1186 1186 1186 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 1107 72 1240 1240 1240 714 714 714 1240 1240 1240 1240 1240 714 714 714 714 714 1240 1240 1240 1240 1240 714 714 714 714 714 1240 1240 1240 1240 1240 714 714 714 714 714 1240 1240 1240 714 714 714 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 1076 831 831 831 831 831 831 831 831 831 831 831 831 831 831 831 831 831 831 831 831 831 642 642 642 642 642 642 642 642 642 642 642 642 642 1493 1493 1493 642 642 642 642 642 1493 1493 1493 1493 1493 642 642 642 1493 1493 1493 1493 1493 1493 1493 1493 1493 1493 64 1493 1493 1493 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 1223 804 804 804 804 804 804 804 804 804 804 804 804 804 804 804 804 804 804 804 804 804 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933 933

56 933 933 933

48

1700 1600 1500 1400 1300 1200 1100 1000 900 800 700 Wavenumber (cm-1)

Latest Revision: 07/30/15 SWGDRUG.org/monographs.htm Page 6 of 7 5-Methoxy-DALT The Drug Enforcement Administration's Special Testing and Research Laboratory generated this monograph using structurally confirmed reference material.

4. ADDITIONAL RESOURCES

http://en.wikipedia.org/wiki/5-MeO-DALTWikipedia

http://forendex.southernforensic.org/index.php/detail/index/1115Forendex

Latest Revision: 07/30/15 SWGDRUG.org/monographs.htm Page 7 of 7