Details of the Drug

General Information of Drug (ID: DMACMLO)

Drug Name
LYSERGIC ACID DIETHYLAMIDE
Synonyms
Lysergide; D-Lysergic acid diethylamide; Delysid; D-Lsd; N,N-Diethyllysergamide; Lysergamid; 50-37-3; Lysergsaeurediaethylamid; Cubes; Pearly gates; Heavenly Blue; Lysergaure diethylamid; Royal blue; N,N-Diethyl-D-lysergamide; LSD (alkaloid); Lysergidum; Wedding bells; Lysergsauerediaethylamid; Lysergic acid diethylamide-25; LSD 25; Lysergidum [INN-Latin]; LSD-25; Lisergide [DCIT]; Lysergamide, N,N-diethyl-; Ubergluben; Clearlight; Sunshine; Cupcakes; Greenies; Barrels; Yellows; Trippers; Microdots; Spoonies
Indication
Disease Entry ICD 11 Status REF
Addictive disorder 6C50-6C5Z Withdrawn from market [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 323.4
Logarithm of the Partition Coefficient (xlogp) 3
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Absorption
The drug is rapidly absorbed []
Half-life
The concentration or amount of drug in body reduced by one-half in 3 hours [2]
Metabolism
The drug is metabolized via the hepatic []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.03313 micromolar/kg/day [3]
Chemical Identifiers
Formula
C20H25N3O
IUPAC Name
(6aR,9R)-N,N-diethyl-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
Canonical SMILES
CCN(CC)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
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
Cross-matching ID
PubChem CID
5761
ChEBI ID
CHEBI:6605
CAS Number
50-37-3
DrugBank ID
DB04829
TTD ID
D0M7LV

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
5-HT 1A receptor (HTR1A) TTSQIFT 5HT1A_HUMAN Inhibitor [4]
5-HT 2A receptor (HTR2A) TTJQOD7 5HT2A_HUMAN Inhibitor [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
5-hydroxytryptamine receptor 2B (HTR2B) OTM1AD9J 5HT2B_HUMAN Protein Interaction/Cellular Processes [6]
5-hydroxytryptamine receptor 6 (HTR6) OT8GTDDY 5HT6R_HUMAN Protein Interaction/Cellular Processes [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Addictive disorder
ICD Disease Classification 6C50-6C5Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
5-HT 1A receptor (HTR1A) DTT HTR1A 2.18E-01 -0.11 -0.51
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 17).
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
4 Stereoselective LSD-like activity in a series of d-lysergic acid amides of (R)- and (S)-2-aminoalkanes. J Med Chem. 1995 Mar 17;38(6):958-66.
5 C-(4,5,6-trimethoxyindan-1-yl)methanamine: a mescaline analogue designed using a homology model of the 5-HT2A receptor. J Med Chem. 2006 Jul 13;49(14):4269-74.
6 Pharmacokinetic and pharmacodynamic evaluation of 5-methoxy-2-aminoindane (MEAI): A new binge-mitigating agent. Toxicol Appl Pharmacol. 2018 Mar 15;343:29-39. doi: 10.1016/j.taap.2018.02.009. Epub 2018 Feb 16.
7 N'-(arylsulfonyl)pyrazoline-1-carboxamidines as novel, neutral 5-hydroxytryptamine 6 receptor (5-HT?R) antagonists with unique structural features. J Med Chem. 2011 Oct 27;54(20):7030-54. doi: 10.1021/jm200466r. Epub 2011 Sep 26.