CAS 50-37-3|CAS 89-77-0|Blue mist|Gelatin chips|N,n-diethyllysergamide|N,N-Diethyl-6-methyl-9,10-didehydroergoline-8-carboxamide|Wedges|California sunshine|(+)-LSD|Lysergide|Blotter acid|Wedding bel...

General Information

Structure

Molecular Formula

C₂₀H₂₅N₃O

Molecular Mass

323.432

Exact Mass

323.19976244

Charge

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

Canonic Smiles

CCN(C(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)CC

Isomeric Smiles

O=C(N(CC)CC)[C@H]1CN([C@H]2C(=C1)c1c3c(C2)c[nH]c3ccc1)C

Calculated Properties

JChem

Acid pKa

17.018362

H Acceptors

H Donor

LogD (pH = 5.5)

-0.15770875

LogD (pH = 7.4)

1.6029848

Log P

2.281515

Molar Refractivity

98.7347

Polarizability

38.704967

Polar Surface Area

39.34

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

3.3

LOG S

-3.08

Solubility (Water)

2.70e-01 g/l

Data Source

Names and Identifiers

Synonyms

ScapesCoffeinumLysergic acid amideD-LSDWindow paneWedding bellsFlatsWedgesYellowsLSD-25FiftyBig fBlue starLysergaure diethylamidD-lysergic acid diethylamideLucy in the sky with diamondsTrippersBeastLysergideWhite lightCherry topCalifornia sunshineLysergamidMean greenClearlightSugarLysergamideChiefPurple microdotOrange sunshineBlue mistBlotter acidLysergidum [inn-latin]D-lysergic acid dethylamideChocolate chipsGelatin chipsN,n-diethyllysergamideN,N-Diethyl-6-methyl-9,10-didehydroergoline-8-carboxamideLysergic acid diethylamide-25Lysergic Acid DiethylamideThe hawkD-lysergic acid n,n-diethylamideStrawberry fields9,10-Didehydro-N,N-diethyl-6-methylergoline-8b-carboxamideDelysidUbergluben(+)-LSDDextrolysergic acid diethylamideTABSContact lensHeavenly blueBlue acidBarrelsCupcakesBart simpsonSunshineMicrodotsMellow yellowSpooniesDomesD-LSD-25ErgineBrown dotsPurple hazeGreeniesN,n-diethyl-d-lysergamideFrogsRoyal blueBartmanDiethylamid kyseliny lysergove [czech]LSDBlue cheerZENAcidn,n-diethyl-(+)-lysergamidePearly gatesTMAOwsleyPaper acid(+)-lysergic acid diethylamideOrange wedgesCubesSugar lumpOrange mushroomLysergic acid diethylamide
''N'',''N''- diethyl- D- lysergamideLSD-25,
lysergidD
D-lysergic acid diethyl amidDLysergic Acid DiethylamideLysergide(8β)-9,10-Didehydro-N,N-diethyl-6-methylergoline-8-carboxamideacid

IUPAC name

(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 (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 (4R,7R)-N,N-diethyl-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

IUPAC Traditional name

lysergic acid diethylamide (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

Names and Identifiers

Registration numbers

PubChem CID

5761

PubChem SID

4650639716096780524896390

CAS Number

MDL Number

EC Number

Chemspider ID

CHEMBL

Unique Ingredient Identifier

8NA5SWF92O

CHEBI ID

6605

Wikipedia Title

Lysergic_acid_diethylamide

DrugBank ID

DB04829

IUPHAR ligand ID

Registration numbers

Properties

Product Information

Certificate of Analysis

Download link

Purity

97%

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Wikipedia

Lysergic_acid_diethylamide

Sigma Aldrich

L7007

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

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]

TRC

L488010

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

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• 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

• 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

• Hoffer, et al.: Clin. Pharmacol. Ther., 6, 183 (1965)

• Steiner, U., et al.: Planta, 224, 533 (1965)

• Mey, G., et al.: Mol. Microbiol., 46, 305 (1965)

• Keller, U., et al.: Biochemistry, 27, 6164 (1965)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

IUPAC Traditional name

lysergic acid diethylamide (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

Registration numbers

PubChem CID

5761

PubChem SID

4650639716096780524896390

CAS Number

MDL Number

EC Number

Chemspider ID

CHEMBL

Unique Ingredient Identifier

8NA5SWF92O

CHEBI ID

6605

Wikipedia Title

Lysergic_acid_diethylamide

DrugBank ID

DB04829

IUPHAR ligand ID

Molecule Details

Wikipedia

Lysergic_acid_diethylamide

Sigma Aldrich

L7007

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

DrugBank

DB04829

Drug Groups

illicit; withdrawn

Description

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]

• 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]

TRC

L488010

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

References

PubChem Literature

From Data Sources

• 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

• 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

• 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

• Hoffer, et al.: Clin. Pharmacol. Ther., 6, 183 (1965)

• Steiner, U., et al.: Planta, 224, 533 (1965)

• Mey, G., et al.: Mol. Microbiol., 46, 305 (1965)

• Keller, U., et al.: Biochemistry, 27, 6164 (1965)

Bioactivity

PubChem BioAssay

Properties

Product Information

Certificate of Analysis

Download link

Purity

97%

Molecule

ID:4373