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Creative Commons Attribution-ShareAlike 3.0 United States Inherent Properties, Identifiers and References
ChemSpider ID: 5558
Empirical Formula: C20H25N3O
Molecular Weight: 323.432
Nominal Mass: 323 Da
Average Mass: 323.432 Da
Monoisotopic Mass: 323.199762 Da
Systematic Name:
SMILES: O=C(N(CC)CC)[C@@H]3/C=C2/c4cccc1c4c(cn1)C[C@H]2N(C3)C
InChI: InChI=1/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-RDTXWAMCBY
Creative Commons Attribution-ShareAlike 3.0 United States (Details...) Original Reference(s)
Lysergic acid diethylamide , LSD, LSD-25, or acid, is a semisynthetic psychedelic drug of the ergoline family. Probably the most widely known psychedelic, it has been used mainly as a recreational drug, an entheogen, and a tool to supplement various practices for transcendence, including in meditation, psychonautics, art projects, and illicit (though at one time legal) psychedelic therapy, whether self-administered or not. It is synthesized from lysergic acid derived from ergot, a grain fungus that typically grows on rye and was first synthesized by Swiss chemist Albert Hofmann. The short form LSD comes from its early codename ''LSD-25'', which is an abbreviation for the German "Lysergsäure-diethylamid" followed by a sequential number. LSD is sensitive to oxygen, ultraviolet light, and chlorine, especially in solution, though its potency may last for years if it is stored away from light and moisture at low temperature. In pure form it is colorless, odorless, and mildly bitter. LSD is typically delivered orally, usually on a substrate such as absorbent blotter paper, a sugar cube, or gelatin. In its liquid form, it can be administered by intramuscular or intravenous injection. The threshold dosage level needed to cause a psychoactive effect on humans is of the order of 20 to 30 µg (micrograms). Introduced by Sandoz Laboratories as a drug with various psychiatric uses, LSD quickly became a therapeutic agent that appeared to show great promise. However, the extra-medicinal use of the drug in Western society during the mid-twentieth century led to a political firestorm that resulted in the banning of the substance. A number of organizations—including the Beckley Foundation, MAPS, Heffter Research Institute and the Albert Hofmann Foundation—exist to fund, encourage and coordinate research into its medicinal uses. Read more... or Edit at Wikipedia...
Creative Commons Attribution-ShareAlike 3.0 United States Disclaimer (Details...) Supplemental Information

User Data

  • experimental physchem properties
    • Melting Point: 80 - 85 C
  • miscellaneous
    • Appearance: crystalline solid
    • Stability: Stable. Incompatible with strong oxidizing agents.
    • Toxicity: IVN-RAT LD50 16 mg kg-1, ORL-BWD LD50 1.8 mg kg-1
    • Safety: Regulated drug. Do not use without adequate training. Safety glasses,gloves, good ventilation. Note that the toxic dose may be extremely low.
(Details...) Names and Synonyms Creative Commons Attribution-ShareAlike 3.0 United States

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(+)-LSD
(8beta)-N,N-diethyl-6-methyl-9,10-didehydroergoline-8-carboxamide
200-033-2[EINECS]
50-37-3[RN]
9,10-Didehydro-N,N-diethyl-6-methylergoline-8b-carboxamide
9,10-Didehydro-N,N-diethyl-6-methyl-ergoline-8-beta-carboxamide
Blotter Acid
Blue Acid
Blue Cheer
Blue Mist
Blue Star
D-Lysergic acid diethylamide
Ergoline-8beta-carboxamide, 9,10-didehydro-N,N-diethyl-6-methyl-
Ergoline-8-beta-carboxamide, 9,10-didehydro-N,N-diethyl-6-methyl-
Ergoline-8-carboxamide, 9,10-didehydro-N,N-diethyl-6-methyl-, (8beta)-
LSD
LYSERGIC ACID DIETHYLAMIDE
Lysergide
Lysergsaure Diethylamid
N,N-Diethyl-D-lysergamide
(+)-Lysergic acid diethylamide
4-25-00-00939 (Beilstein Handbook Reference)
Delysid[Wiki]
Diethylamid kyseliny lysergove[Czech]
Ergoline-8b-carboxamide, 9,10-didehydro-N,N-diethyl-6-methyl- (8CI)
Lisergide [DCIT]
Lisergido[Spanish]
Lysergamid
Lysergamide, N,N-diethyl-
Lysergaure diethylamid
Lysergic acid diethylamide-25
Lysergide [BAN:DCF:INN]
Lysergide LSD
LYSERGIDE, L-
Lysergidum[Latin]
Lysergsaeurediaethylamid
N,N-Diethyllysergamide
(Details...) Database ID(s) Creative Commons Attribution-ShareAlike 3.0 United States

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LSD-25
BRN 0094179
C07542
DEA No. 7315
HSDB 3920
LSD 25
(Details...) Predicted Properties
LogP: ACD/LogP: 2.74
XLogP: 2.10
# of Rule of 5 Violations: 0
ACD/LogD (pH 5.5): 0.5 ACD/LogD (pH 7.4): 2.19
ACD/BCF (pH 5.5): 1 ACD/BCF (pH 7.4): 20.3
ACD/KOC (pH 5.5): 4.27 ACD/KOC (pH 7.4): 210.6
#H bond acceptors: 4 #H bond donors: 1
#Freely Rotating Bonds: 3 Polar Surface Area: 28.48 Å2
Index of Refraction: 1.651 Molar Refractivity: 97.22 cm3
Molar Volume: 266 cm3 Polarizability: 38.54 10-24cm3
Surface Tension: 55.9 dyne/cm Density: 1.21 g/cm3
Flash Point: 281.2 °C Enthalpy of Vaporization: 81.91 kJ/mol
Boiling Point: 541.3 °C at 760 mmHg Vapour Pressure: 8.82E-12 mmHg at 25°C
Descriptors: 0, 0, 0, 1, 1, 0, 0, 3, 0, 0, 0, 0, 13, 3, 6, 1, 9, 2, 1, 0, 2, 0, 0, 0
CategoryTargetPDB CodeLASSO Score
Nuclear Hormone ReceptorsPPARg, peroxisome proliferator activated receptor1fm90.03
Other EnzymesInhA, enoyl ACP reductase1p440.02
KinasesPDGFrb, platelet derived growth factor receptor kinaseN/A0.02
KinasesSRC, tyrosine kinase SRC2src0.01
Other EnzymesHMGR, hydroxymethylglutaryl-CoA reductase1hw80.01
Serine ProteasesThrombin1ba80.01
Other EnzymesHIVPR, HIV protease1hpx0.01
MetalloenzymesPDE5, phosphodiesterase 51xp00.01
Nuclear Hormone ReceptorsMR, mineralocorticoid receptor2aa20.01
MetalloenzymesACE, angiotensin-converting enzyme1o860.01
Other EnzymesPARP, poly(ADP-ribose) polymerase1efy0.01
Other EnzymesPNP, purine nucleoside phosphorylase1b8o0.00
Other EnzymesAmpC, AmpC beta-lactamase1xgj0.00
Nuclear Hormone ReceptorsER, estrogen receptor; agonist1l2i0.00
Nuclear Hormone ReceptorsPR, progesterone receptor1sr70.00
Folate EnzymesDHFR, dihydrofolate reductase3dfr0.00
KinasesVEGFr2, vascular endothelial growth factor receptor1vr20.00
Other EnzymesGPB, glycogen phosphorylase1a8i0.00
Other EnzymesSAHH, S-adenosyl-homocysteine hydrolase1a7a0.00
KinasesFGFr1, fibroblast growth factor receptor kinase1agw0.00
Other EnzymesCOX-2, cyclooxygenase-21cx20.00
Other EnzymesALR2, aldose reductase1ah30.00
KinasesCDK2, cyclindependent kinase 21ckp0.00
Nuclear Hormone ReceptorsRXRa, retinoic X receptor R1mvc0.00
Other EnzymesNA, neuraminidase1a4g0.00
KinasesTK, thymidine kinase1kim0.00
MetalloenzymesADA, adenosine deaminase1stw0.00
KinasesP38 MAP, P38 mitogen activated protein1kv20.00
Nuclear Hormone ReceptorsAR, androgen receptor1xq20.00
Serine ProteasesFXa, factor Xa1f0r0.00
Folate EnzymesGART, glycinamide ribonucleotide transformylase1c2t0.00
MetalloenzymesCOMT, catechol O-methyltransferase1h1d0.00
KinasesHSP90, human heat shock protein 901uy60.00
Other EnzymesHIVRT, HIV reverse transcriptase1rt10.00
Other EnzymesAChE, acetylcholinesterase1eve0.00
KinasesEGFr, epidermal growth factor receptor1m170.00