(4R,7R)-N,N-diethyl-6-methyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide

• ChemBase ID: 4373
• Molecular Formular: C20H25N3O
• Molecular Mass: 323.432
• Monoisotopic Mass: 323.19976244
• SMILES: O=C(N(CC)CC)[C@H]1CN([C@H]2C(=C1)c1c3c(C2)c[nH]c3ccc1)C
• Canonical SMILES: CCN(C(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)CC
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,7R)-N,N-diethyl-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide; (4R,7R)-N,N-diethyl-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide; (4R,7R)-N,N-diethyl-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
• IUPAC Traditional name: (4R,7R)-N,N-diethyl-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide; lysergic acid diethylamide
• Synonyms: (8β)-9,10-Didehydro-N,N-diethyl-6-methylergoline-8-carboxamide; Lysergic Acid Diethylamide; Lysergide; Lysergic acid diethylamide; LSD-25,; lysergidD; ; D-lysergic acid diethyl amidD; ; ''N'',''N''- diethyl- D- lysergamide; N,N-Diethyl-6-methyl-9,10-didehydroergoline-8-carboxamide; n,n-diethyl-(+)-lysergamide; Lysergidum [inn-latin]; Lysergide; Diethylamid kyseliny lysergove [czech]; Dextrolysergic acid diethylamide; Delysid; D-lysergic acid n,n-diethylamide; D-lysergic acid diethylamide; D-lysergic acid dethylamide; D-LSD-25; D-LSD; Cupcakes; Cubes; Contact lens; Coffeinum; Clearlight; Chocolate chips; Chief; Cherry top; California sunshine; Brown dots; Blue star; Blue mist; Microdots; Mellow yellow; Mean green; Lysergic acid diethylamide-25; Lysergic acid amide; Lysergaure diethylamid; Lysergamide; Lysergamid; Lucy in the sky with diamonds; Heavenly blue; Greenies; Gelatin chips; Frogs; Flats; Fifty; Ergine; Domes; Lysergic Acid Diethylamide; LSD; LSD-25; (+)-LSD; (+)-lysergic acid diethylamide; 9,10-Didehydro-N,N-diethyl-6-methylergoline-8b-carboxamide; Acid; Barrels; Bart simpson; Bartman; Beast; Big f; Blotter acid; Blue acid; Blue cheer; ZEN; Yellows; Window pane; White light; Wedges; Wedding bells; Ubergluben; Trippers; TMA; The hawk; TABS; Sunshine; Sugar lump; Sugar; Strawberry fields; Spoonies; Scapes; Royal blue; Purple microdot; Purple haze; Pearly gates; Paper acid; Owsley; Orange wedges; Orange sunshine; Orange mushroom; N,n-diethyllysergamide; N,n-diethyl-d-lysergamide; acid

Database IDs

• CAS Number: 89-77-0; 50-37-3
• EC Number: 200-033-2
• MDL Number: MFCD00135795
• PubChem SID: 46506397; 24896390; 160967805
• PubChem CID: 5761
• CHEBI ID: 6605
• CHEMBL: 263881
• Chemspider ID: 5558
• DrugBank ID: DB04829
• IUPHAR ligand ID: 17
• Unique Ingredient Identifier: 8NA5SWF92O
• Wikipedia Title: Lysergic_acid_diethylamide

CALCULATED PROPERTIES

JChem

• Acid pKa: 17.018362
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.15770875
• LogD (pH = 7.4): 1.6029848
• Log P: 2.281515
• Molar Refractivity: 98.7347 cm^3
• Polarizability: 38.704967 Å^3
• Polar Surface Area: 39.34 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.3
• LOG S: -3.08
• Solubility (Water): 2.70e-01 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol; Pyridine
• Apperance: Brown Solid
• Melting Point: 80-85 °C (176-185°F); 91-93°C
• Hydrophobicity(logP): 2.95 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer
• RTECS: KE4100000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 26/27/28-40
• Safety Statements: 22-28-36-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330-H351
• GHS Precautionary statements: P260-P264-P280-P284-P302 + P350-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Drug Control: USDEA Schedule I; Home Office Schedule 1; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C

Pharmacology Properties

• Admin Routes: Oral, Intravenous, Ocular, Intramuscular
• Dependency Liability: Very low
• Excretion: Renal
• Half Life: 3–5 hours
• Metabolism: Hepatic
• Legal Status: CD (UK); Schedule 9 (Australia); Schedule I (US); Schedule III (Canada)
• Pregnancy Category: C (US)
• Gene Information: human ... DRD2(1813), HTR1A(3350), HTR2A(3356), HTR2C(3358), HTR6(3362)rat ... Htr1a(24473), Htr2a(29595), Htr2c(25187), Htr7(65032)

Product Information

• Purity: 97%

DETAILS

DrugBank - DB04829

• Drug Groups: illicit; withdrawn
• Description: Debate continues over the nature and causes of chronic flashbacks. Explanations in terms of LSD physically remaining in the body for months or years after consumption have been discounted by experimental evidence. Some say HPPD is a manifestation of post-traumatic stress disorder, not related to the direct action of LSD on brain chemistry, and varies according to the susceptibility of the individual to the disorder. Many emotionally intense experiences can lead to flashbacks when a person is reminded acutely of the original experience. However, not all published case reports of chronic flashbacks appear to describe an anxious hyper-vigilant state reminiscent of post-traumatic stress disorder.
• Toxicity: Estimates for the lethal dosage (LD50) of LSD range from 200 μg/kg to more than 1 mg/kg of human body mass, though most sources report that there are no known human cases of such an overdose.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Half Life: 3 hours
• References: GREINER T, BURCH NR, EDELBERG R: Psychopathology and psychophysiology of minimal LSD-25 dosage; a preliminary dosage-response spectrum. AMA Arch Neurol Psychiatry. 1958 Feb;79(2):208-10. [Pubmed] ; AGHAJANIAN GK, BING OH: PERSISTENCE OF LYSERGIC ACID DIETHYLAMIDE IN THE PLASMA OF HUMAN SUBJECTS. Clin Pharmacol Ther. 1964 Sep-Oct;5:611-4. [Pubmed] ; Papac DI, Foltz RL: Measurement of lysergic acid diethylamide (LSD) in human plasma by gas chromatography/negative ion chemical ionization mass spectrometry. J Anal Toxicol. 1990 May-Jun;14(3):189-90. [Pubmed] ; Nichols DE: Hallucinogens. Pharmacol Ther. 2004 Feb;101(2):131-81. [Pubmed] ; Jacobs BL, Heym J, Rasmussen K: Raphe neurons: firing rate correlates with size of drug response. Eur J Pharmacol. 1983 Jun 3;90(2-3):275-8. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - L7007

Biochem/physiol Actions
Potent hallucinogen; non-selective serotonin receptor agonist.

Toronto Research Chemicals - L488010

Potent hallucinogen; non-selective serotonin receptor agonist. Has been used experimentally as adjunct in study and treatment of mental disorders.Controlled substance.

REFERENCES

• GREINER T, BURCH NR, EDELBERG R: Psychopathology and psychophysiology of minimal LSD-25 dosage; a preliminary dosage-response spectrum. AMA Arch Neurol Psychiatry. 1958 Feb;79(2):208-10. Pubmed
• AGHAJANIAN GK, BING OH: PERSISTENCE OF LYSERGIC ACID DIETHYLAMIDE IN THE PLASMA OF HUMAN SUBJECTS. Clin Pharmacol Ther. 1964 Sep-Oct;5:611-4. Pubmed
• Papac DI, Foltz RL: Measurement of lysergic acid diethylamide (LSD) in human plasma by gas chromatography/negative ion chemical ionization mass spectrometry. J Anal Toxicol. 1990 May-Jun;14(3):189-90. Pubmed
• Jacobs BL, Heym J, Rasmussen K: Raphe neurons: firing rate correlates with size of drug response. Eur J Pharmacol. 1983 Jun 3;90(2-3):275-8. Pubmed
• Nichols DE: Hallucinogens. Pharmacol Ther. 2004 Feb;101(2):131-81. Pubmed
• Hoffer, et al.: Clin. Pharmacol. Ther., 6, 183 (1965)
• Keller, U., et al.: Biochemistry, 27, 6164 (1965)
• Mey, G., et al.: Mol. Microbiol., 46, 305 (1965)
• Steiner, U., et al.: Planta, 224, 533 (1965)