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Psychedelic drug
Pharmaceutical compound
DAM-57 Other names DAM-57; N ,N -Dimethyllysergamide; DAM; Lysergic acid dimethylamide Routes of administration Oral [ 1] Legal status
(6aR ,9R )-N ,N -dimethyl-7-methyl-4,6,6a,7,8,9- hexahydroindolo- [4,3-fg] quinoline- 9-carboxamide
CAS Number PubChem CID ChemSpider UNII CompTox Dashboard (EPA ) Formula C 18 H 21 N 3 O Molar mass 295.386 g·mol−1 3D model (JSmol )
O=C(N(C)C)[C@@H]3C=C2c4cccc1c4c(c[nH]1)C[C@H]2N(C3)C
InChI=1S/C18H21N3O/c1-20(2)18(22)12-7-14-13-5-4-6-15-17(13)11(9-19-15)8-16(14)21(3)10-12/h4-7,9,12,16,19H,8,10H2,1-3H3/t12-,16-/m1/s1
Y Key:FWHSERNVTGTIJE-MLGOLLRUSA-N
Y
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DAM-57 , also known as N ,N -dimethyllysergamide (DAM ) or as lysergic acid dimethylamide , is a derivative of ergine . There has been a single report of observing N,N-dimethyl-D-lysergamide in the illicit drug market.[ 2] This compound did induce autonomic disturbances at oral levels of some 10 times the dose required for lysergic acid diethylamide (LSD), presumably in the high hundreds of micrograms. There is some disagreement as to whether there were psychic changes observed.[ 1] It was first described in the scientific literature by Albert Hofmann and colleagues by 1955.[ 3]
No ring subs. 4-Hydroxytryptamines 5-Hydroxytryptamines 5-Methoxytryptamines Other ring subs. α-Alkyltryptamines Others
Ergolines /lysergamides (e.g., LSD )
Ibogalogs (e.g., ibogainalog , tabernanthalog , Pharm-136 )
O -Methylnordehydrobufotenine
Partial ergolines (e.g., NDTDI , RU-28306 , CT-5252 )
Piperidinylethylindoles (e.g., pip-T )
Pyrrolidinylethylindoles (e.g., pyr-T , 5-MeO-pyr-T )
Pyrrolidinylmethylindoles (e.g., MPMI , 4-HO-MPMI (lucigenol) , 5-MeO-MPMI , MSP-2020 )
Tetrahydropyridinylindoles (e.g., RU-28253 (5-MeO-THPI) , NEtPhOH-THPI )
Others: 2C-B-AN
2C-DB
2C-G-x (e.g., 2C-G-3 , 2C-G-5 )
β-Keto-2C-B (βk-2C-B)
β-Keto-2C-I (βk-2C-I)
β-Methyl-2C-B (BMB)
(e.g., BOB , BOD , BOHB )
(e.g., HOT-2 , HOT-7 , HOT-17 )
N -Ethyl-2C-B
(e.g., 2CB-2-EtO , 2CD-2-EtO , 2CD-5-EtO , 2CE-5-EtO , 2CE-5iPrO , 2CT-5-EtO , 2CT2-2-EtO , 2CT7-2-EtO , ASR-2001 (2CB-5-PrO) )
Others
25B-NAcPip
2-DM-DOM
4-HA
5-DM-DOM
Benzofurans (e.g., 5-APB , 5-APDB , 6-APB , 6-APDB , F , F-2 , F-22 )
Benzothiophenes (e.g., 5-APBT , 6-APBT )
BMB-202
CT-5172
DMAs (e.g., 2,4-DMA , 3,4-DMA )
Fenfluramine
MMA (3-MeO-4-MA)
Norfenfluramine
(e.g., 25D-NM-NDEAOP , DOB-NDEPA , DOI-NDEPA , DOM-NDEPA , DOTFM-NDEPA , M-NDEPA , TMA-2-NDEPA )
PMA (4-MA)
Thio-2Cs (e.g., 2C-5-TOET )
Thio-DOx (e.g., 2-TOM , 5-TOET , 5-TOM , TOMSO )
(e.g., TMA-3 , TMA-4 , TMA-5 )
ZDCM-04 (DOC-fenethylline)
1-Aminomethylindanes (e.g., 2CB-Ind , jimscaline )
2-Aminoindanes (e.g., DOM-AI )
3-Benzazepines (e.g., lorcaserin )
3-Phenylpiperidines (e.g., LPH-5 , LPH-48 )
Benzocyclobutenes (e.g., 2CBCB-NBOMe , TCB-2 , tomscaline )
Benzoxepins (e.g., BBOX , IBOX , TFMBOX )
DMBMPP (juncosamine)
Ergolines /lysergamides (e.g., LSD )
Partial ergolines (e.g., NDTDI , DEIMDHPCA , DEMPDHPCA , DEMTMPDHPCA , DEMNDHPCA )
Phenylcyclopropylamines (e.g., DMCPA , TMT )
Phenyloxazolamines (aminorexes ) (e.g., 2C-B-aminorex )
Pyridopyrroloquinoxalines (e.g., IHCH-7113 )
Z3517967757
ZC-B
Others
9-Oxaergolines (e.g., RU-29717 )
γ-Carbolines (e.g., tiflucarbine )
Arylpiperazines (e.g., 2C-B-PP , 2-NP , mCPP , MK-212 , ORG-12962 , pCPP , pFPP , quipazine , TFMPP , VCU-1012 )
Dihydrobenzoxazines (e.g., efavirenz )
Phenoxyethylamines (e.g., CT-4719 , ORG-37684 )
Pyridopyrroloquinoxalines (e.g., IHCH-7113 )
Quinazolinylethylamines (e.g., RH-34 )
Natural sources
Tryptamines: Acacia spp. (e.g., Acacia acuminata , Acacia confusa )
Ayahuasca and vinho de Jurema (e.g., Psychotria viridis (chacruna) , Dipolopterys cabrerana (chaliponga, chacruna) , Mimosa tenuiflora (Mimosa hostilis ; jurema) )
Brosimum (e.g., Brosimum acutifolium (takini) )
Hallucinogenic snuffs (e.g., Anadenanthera peregrina (yopo, jopo, cohoba, parica, ebene) , Anadenanthera colubrina (vilca, cebil) )
Incilius alvarius (Bufo alvarius ; Colorado River toad, Sonoran Desert toad; bufo)
Psilocybin-containing mushrooms (magic mushrooms, shrooms) (e.g., Psilocybe cubensis , Psilocybe mexicana (teonanacatl) )
Lysergamides: Achnatherum robustum (sleepy grass)
Epichloë spp.
Ergot (Claviceps ) (e.g., Claviceps purpurea , Claviceps paspali )
Morning glory (Convolvulaceae) seeds (e.g., Ipomoea tricolor (tlitliltzin, badoh negro; Ipomoea violacea ) , Ipomoea corymbosa (coaxihuitl, ololiúqui; Rivea Corymbosa , Turbina Corymbosa ) , Argyreia nervosa (Hawaiian baby woodrose; HBWR) )
Periglandula spp. (e.g., Periglandula ipomoeae , Periglandula clandestina )
Ergolines (incl. lysergines )Clavines (6,8-dimethylergolines)Lysergamides (lysergic acid amides)
Psychedelic lysergamides: 1B-LSD
1BP-LSD
1Bz-LSD
1cP-AL-LAD
1cP-LSD
1cP-MiPLA
1D-AL-LAD
1D-LSD
1DD-LSD
1F-LSD
1Fe-LSD
1H-LSD
1P-AL-LAD
1P-ETH-LAD
1P-LSD
1P-MiPLA
1S-LSD
1SB-LSD (1BS-LSD)
1T-AL-LAD
1T-LSD
1V-LSD
2,3-Dihydro-LSD
AL-LAD
ALA-10 (1-acetyl-LAE)
ALD-52 (1-acetyl-LSD)
BU-LAD
CPM-LAD
CYP-LAD
Diallyllysergamide (DAL)
Dimethyllysergamide (DAM-57)
Diisopropyllysergamide (DiPLA)
Dipropyllysergamide (DPL)
Ergine (lysergic acid amide; LSA; LA-111; lysergamide)
Ergometrine (ergonovine, ergobasine)
ETH-LAD
Ethylcyclopropyllysergamide (EcPLA)
Ethylisopropyllysergamide (EiPLA)
Ethylpropyllysergamide (EPLA; LEP-57)
Ethyltrifluoroethyllysergamide (ETFELA)
IP-LAD
Isoergine (isolysergic acid amide; iso-LSA; iso-LA; isolysergamide)
Isopropyllysergamide (iPLA; LAiP)
Methylpropyllysergamide (LAMPA, LMP-55)
Lysergic acid diethylamide (LSD; d -LSD; lysergide)
Lysergic acid ethylamide (LAE-32, LAE)
Lysergic acid hydroxyethylamide (LSH, LAH)
Lysergic acid methylamide (LAM)
Lysergic acid methylethylamide (LME-54)
Lysergic acid morpholide (LSM-775)
Lysergic acid propylamide (LAP)
Lysergic acid pyrrolidide (LPD-824)
Lysergic acid 2-butylamide (LSB)
Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ, LA-Azetidine)
Lysergic acid 2-pentylamide (2-LSP)
Lysergic acid 3-pentylamide (LSP, 3-LSP)
Methylergometrine (methylergonovine, methylergobasine; Methergine)
Methylisopropyllysergamide (MiPLA)
Methysergide (1-methylmethylergonovine; UML-491)
MLA-74 (1-methyl-LAE)
MLD-41 (1-methyl-LSD)
MPD-75 (1-methyllysergic acid pyrrolidide)
NBOMe-LAD
OML-632 (1-hydroxymethyl-LSD)
PARGY-LAD
PRO-LAD
TRALA-12 (didehydro-LSD; DDH-LSD)
Ergopeptines (peptide ergolines)Partial ergolines Related compounds Natural sources