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Addictive disorder	6C50-6C5Z	Withdrawn from market	[1]

• Affected Organisms: Humans and other mammals
• Drug Type: Small molecular drug
• #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
  UNII: 8NA5SWF92O
  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 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

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.