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Dimethyllysergamide: Difference between revisions

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{{short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 417014631
| 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
| 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
| image = DAM-57.svg
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| legal_CA =
| legal_CA =
| legal_UK =
| legal_UK =
| legal_US = [[Schedule I]]
| legal_US = Schedule I
| legal_status = Controlled in the [[United States]] via the [[Federal Analog Act]] but only if it is intended for human consumption.
| 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]]
| routes_of_administration = [[Wiktionary:oral|Oral]]


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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 172668
| ChemSpiderID = 172668
| CAS_number = 4238-84-0
| CAS_number_Ref = {{Cascite|correct|CAS}}


<!--Chemical data-->
<!--Chemical data-->
| C=18 | H=21 | N=3 | O=1
| 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
| molecular_weight = 295.39 g/mol
⚫
| smiles = O=C(N(C)C)[C@@H]3/C=C2/c4cccc1c4c(cn1)C[C@H]2N(C3)C
| InChI = 1/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
| InChIKey = FWHSERNVTGTIJE-MLGOLLRUBO
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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
| 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
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}}
}}


'''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. <ref>A. B. Clark, Microgram., 6, 37 (1973)</ref> It may cause [[LSD]]-like effects at doses of 1 milligram or more but this is disputed.
'''''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>


==References==
==References==
{{Reflist}}
{{Reflist}}


{{Hallucinogenic lysergamides}}


{{Hallucinogens}}
{{DEFAULTSORT:Dam-57}}
{{Ergolines}}

[[Category:Lysergamides]]
[[Category:Lysergamides]]


Latest revision as of 13:03, 13 January 2023

Dimethyllysergamide
Clinical data
Other namesDAM-57, Lysergic acid dimethylamide
Routes of
administration		Oral
Legal status
Legal status
Pharmacokinetic data
Metabolismhepatic
Excretionrenal
Identifiers
  • (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
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H21N3O
Molar mass295.386 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 checkY
  • Key:FWHSERNVTGTIJE-MLGOLLRUSA-N checkY
  (verify)

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]

  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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