Dimethyllysergamide: Difference between revisions

Dimethyllysergamide
Clinical data
Other names	DAM-57, Lysergic acid dimethylamide
Routes of; administration	Oral
Legal status
Legal status	US: Schedule I Controlled in the United States via the Federal Analog Act but only if it is intended for human consumption.;
Pharmacokinetic data
Metabolism	hepatic
Excretion	renal
Identifiers
	IUPAC name (6aR,9R)-N,N-dimethyl-7-methyl-4,6,6a,7,8,9- hexahydroindolo- [4,3-fg] quinoline- 9-carboxamide;
CAS Number	4238-84-0 ;
PubChem CID	199478;
ChemSpider	172668 ;
CompTox Dashboard (EPA)	DTXSID30962445 ;
Chemical and physical data
Formula	C18H21N3O
Molar mass	295.386 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(N(C)C)[C@@H]3C=C2c4cccc1c4c(c[nH]1)C[C@H]2N(C3)C;
	InChI 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 ; Key:FWHSERNVTGTIJE-MLGOLLRUSA-N ;
	(verify)

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Latest revision as of 13:03, 13 January 2023

N,N-Dimethyllysergamide or N,N-dimethyl-D-lysergamide (DAM-57) is a derivative of ergine. There has been a single report of observing N,N-dimethyl-D-lysergamide in the illicit drug market.^[1] This compound did induce autonomic disturbances at oral levels of some ten times the dosage required for LSD, presumably in the high hundreds of micrograms. There is some disagreement as to whether there were psychic changes observed.^[2]

References[edit]

^ Clark AB (1973). "Lysergic Acid Diethylamide and Lysergic Acid Dimethylamide". Microgram. 6: 37.
^ Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. p. 26. ISBN 0-9630096-9-9. OCLC 38503252.; "#26. LSD-25". Erowid.

This hallucinogen-related article is a stub. You can help Wikipedia by expanding it.

[1] Clark AB (1973). "Lysergic Acid Diethylamide and Lysergic Acid Dimethylamide". Microgram. 6: 37.

[2] Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. p. 26. ISBN 0-9630096-9-9. OCLC 38503252.; "#26. LSD-25". Erowid.

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@@ Line 1: / Line 1: @@
+{{short description|Chemical compound}}
-{{drugbox |
+{{Drugbox
-| width = 300
+| Watchedfields = changed
+| verifiedrevid = 447574383
+| IUPAC_name = (6a''R'',9''R'')-''N'',''N''-dimethyl-7-methyl-4,6,6a,7,8,9- hexahydroindolo- [4,3-fg] quinoline- 9-carboxamide
 | image = DAM-57.svg
-| IUPAC_name =
+<!--Clinical data-->
-| C=18 | H=21 | N=3 | O=1
+| tradename =
-| molecular_weight =  295.39 g/mol
+| legal_AU =
-| synonyms = DAM-57, Lysergic acid dimethylamide
+| legal_CA =
+| legal_UK =
+| legal_US = Schedule I
+| legal_US_comment = Controlled in the United States via the [[Federal Analog Act]] but only if it is intended for human consumption.
+| routes_of_administration = [[Wiktionary:oral|Oral]]
+<!--Pharmacokinetic data-->
 | metabolism = hepatic
 | excretion = renal
-| legal_AU =
-| legal_CA =
-| legal_UK =
-| legal_US =
-| legal_status =
-| routes_of_administration = [[Wiktionary:oral|Oral]]}}
+<!--Identifiers-->
-'''N,N-Dimethyllysergamide''' (DAM-57) is a derivative of [[ergine]].
+| PubChem = 199478
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 172668
+| CAS_number = 4238-84-0
+| CAS_number_Ref = {{Cascite|correct|CAS}}
+<!--Chemical data-->
-It may cause LSD-like effects at doses of 1 milligram or more but this is disputed.
+| C=18 | H=21 | N=3 | O=1
+| smiles = O=C(N(C)C)[C@@H]3C=C2c4cccc1c4c(c[nH]1)C[C@H]2N(C3)C
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChI = 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
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChIKey = FWHSERNVTGTIJE-MLGOLLRUSA-N
+| synonyms = DAM-57, Lysergic acid dimethylamide
+}}
+'''''N,N''-Dimethyllysergamide''' or '''''N,N''-dimethyl-D-lysergamide''' ('''DAM-57''') is a [[Derivative (chemistry)|derivative]] of [[ergine]]. There has been a single report of observing N,N-dimethyl-D-lysergamide in the illicit drug market.<ref>{{cite journal | vauthors = Clark AB | title = Lysergic Acid Diethylamide and Lysergic Acid Dimethylamide| journal = Microgram | volume = 6 | pages = 37 | date = 1973 }}</ref> This compound did induce autonomic disturbances at oral levels of some ten times the dosage required for [[LSD]], presumably in the high hundreds of micrograms. There is some disagreement as to whether there were psychic changes observed.<ref>{{CiteTiHKAL|pages=26|name-list-style=vanc}}; {{cite web | title = #26. LSD-25 | url = https://www.erowid.org/library/books_online/tihkal/tihkal26.shtml | work = Erowid }}</ref>
-{{pharmacology-stub}}
-{{hallucinogenic lysergamides}}
+==References==
+{{Reflist}}
+{{Hallucinogens}}
+{{Ergolines}}
-[[Category:Psychedelics]]
 [[Category:Lysergamides]]
+{{hallucinogen-stub}}

v t e Ergolines
Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Amesergide Bromocriptine Cabergoline Dihydroergocornine Dihydroergocristine Dihydroergocryptine Dihydroergometrine (Dihydroergonovine, Dihydroergobasine) Dihydroergosine Dihydroergotamine Epicriptine Ergine (LSA; LA-111; Lysergamide) Ergocornine Ergocristine Ergocryptine Ergoloid (Dihydroergotoxine) Ergometrine (Ergonovine, Ergobasine) Ergometrinine Ergostine Ergotamine Ergotoxine Ergovaline Lisuride LY-215,840 LSH Lysergic acid Lysergic acid methyl ester Lysergol Mesulergine Metergoline MIPLA Methysergide Sergolexole
Psychedelic lysergamides	1B-LSD 1cP-LSD 1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD CYP-LAD Diallyllysergamide (DAL) Dimethyllysergamide (DAM-57) ECPLA Ergonovine ETFELA ETH-LAD IP-LAD LAMPA LAE-32 LSD LPD-824 LSM-775 LSH LSD-Pip Lysergic Acid 2-Butylamide Lysergic Acid 2,4-Dimethylazetidide Lysergic Acid 3-Pentylamide Lysergic acid cyclobutylamide Lysergic acid cyclopentylamide Methylergometrine (Methylergonovine, Methylergobasine) MIPLA MLD-41 PARGY-LAD PRO-LAD
Clavines	9-Deacetoxyfumigaclavine C Agroclavine Chanoclavine Chanoclavine II Costaclavin Cycloclavine Elymoclavine Epoxyagroclavine Festuclavine Fumigaclavine A Fumigaclavine B Fumigaclavine C Paliclavine Penniclavine Setoclavine
Other ergolines	Acetergamine CY-208,243 Ergoline Lergotrile Nicergoline Pergolide
Natural sources	Achnatherum robustum (Sleepy Grass) Claviceps spp. (Ergot) Morning glory: Argyreia nervosa (Hawaiian Baby Woodrose), Ipomoea spp.(Morning Glory, Tlitliltzin, Badoh Negro), Rivea corymbosa (Coaxihuitl, Ololiúqui)