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Substance Name: Lysergide [INN:BAN:DCF]
RN: 50-37-3
UNII: 8NA5SWF92O
InChIKey: VAYOSLLFUXYJDT-RDTXWAMCSA-N

Note

  • Semisynthetic derivative of ergot (Claviceps purpurea). It has complex effects on serotonergic systems including antagonism at some peripheral serotonin receptors, both agonist and antagonist actions at central nervous system serotonin receptors, and possibly effects on serotonin turnover. It is a potent hallucinogen, but the mechanisms of that effect are not well understood.

Molecular Formula

  • C20-H25-N3-O

Molecular Weight

  • 323.4375
 

Classification Codes

Classification Codes

  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Hallucinogens
  • Human Data
  • Mutation Data
  • Neurotransmitter Agents
  • Psychotropic Drugs
  • Reproductive Effect
  • Serotonin Agents
  • Serotonin Antagonists
  • Serotonin Receptor Agonists

Superlist Classification Code

  • DEA Schedule I
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Names and Synonyms

Name of Substance

  • LSD
  • Lysergic acid diethylamide
  • Lysergide [INN:BAN:DCF]

MeSH Heading

  • Lysergic acid diethylamide

Synonyms

  • 4-25-00-00939 (Beilstein Handbook Reference)
  • 9,10-Didehydro-N,N-diethyl-6-methyl-ergoline-8-beta-carboxamide
  • Acid [Street Name]
  • BRN 0094179
  • Cubes [Street Name]
  • D-Lsd
  • D-Lysergic acid diethylamide
  • Delysid
  • Diethylamid kyseliny lysergove
  • Diethylamid kyseliny lysergove [Czech]
  • EINECS 200-033-2
  • Ergoline-8-carboxamide, 9,10-didehydro-N,N-diethyl-6-methyl-, (8beta)-
  • Ergoline-8beta-carboxamide, 9,10-didehydro-N,N-diethyl-6-methyl-
  • Heavenly Blue [Street Name]
  • HSDB 3920
  • Lisergide
  • Lisergide [DCIT]
  • Lisergido
  • Lisergido [INN-Spanish]
  • LSD
  • LSD (alkaloid)
  • LSD-25
  • Lysergamid
  • Lysergamide, N,N-diethyl-
  • Lysergaure diethylamid
  • Lysergic acid diethylamide
  • Lysergic acid diethylamide-25
  • Lysergide
  • Lysergidum
  • Lysergidum [INN-Latin]
  • Lysergsaeurediaethylamid
  • Lysergsauerediaethylamid
  • N,N-Diethyl-D-lysergamide
  • N,N-Diethyllysergamide
  • Pearly gates [Street Name]
  • Royal Blue [Street Name]
  • UNII-8NA5SWF92O
  • Wedding bells [Street Name]

Systematic Names

  • Ergoline-8-beta-carboxamide, 9,10-didehydro-N,N-diethyl-6-methyl-
  • Ergoline-8-carboxamide, 9,10-didehydro-N,N-diethyl-6-methyl-, (8beta)-
  • Lysergide
  • N,N-Diethyllysergamide

Superlist Names

  • DEA No. 7315
  • Lysergic acid diethylamide

Registry Numbers

CAS Registry Number

  • 50-37-3

FDA UNII

  • 8NA5SWF92O

System Generated Number

  • 0000050373

Structure Descriptors

InChI

1S/C20H25N3O/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3/t14-,18-/m1/s1

InChIKey

VAYOSLLFUXYJDT-RDTXWAMCSA-N

Smiles

c12c3C4=C[C@H](CN([C@@H]4Cc1c[nH]c2ccc3)C)C(=O)N(CC)CC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 1800ug/kg (1.8mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
guinea pig LD50 subcutaneous 16mg/kg (16mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 137, Pg. 375, 1962.
human TDLo intramuscular 750ng/kg (0.00075mg/kg) BEHAVIORAL: EUPHORIA

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Psychopharmacologia Vol. 3, Pg. 219, 1962.
human TDLo oral 700ng/kg (0.0007mg/kg) BEHAVIORAL: EXCITEMENT Journal of Pharmacology and Experimental Therapeutics. Vol. 120, Pg. 340, 1957.
human TDLo oral 857ng/kg (0.000857mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: ANOREXIA (HUMAN

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 220, 1966.
human TDLo oral 2857ng/kg (0.002857mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 356, 1969.
mouse LD50 intraperitoneal 50mg/kg (50mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 intravenous 46mg/kg (46mg/kg)   International Record of Medicine. Vol. 172, Pg. 702, 1959.
rabbit LD50 intravenous 300ug/kg (0.3mg/kg)   Annals of the New York Academy of Sciences. Vol. 66, Pg. 668, 1957.
rabbit LD50 intravenous 300ug/kg (0.3mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
Annals of the New York Academy of Sciences. Vol. 66, Pg. 668, 1957.
rat LD50 intravenous 16mg/kg (16mg/kg)   International Record of Medicine. Vol. 172, Pg. 702, 1959.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 82.5 deg C   EXP
pKa Dissociation Constant 7.8 (none)   EXP
log P (octanol-water) 2.95 (none)   EXP
Water Solubility 2.100 mg/L 25 EST
Vapor Pressure 9.03E-10 mm Hg 25 EST
Henry's Law Constant 1.53E-16 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 4.16E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.