Details of the Drug-Related molecule(s) Interaction Atlas

General Information of Drug (ID: DMD1SY9)

• Drug Name: bufotenine Drug Info
• Synonyms: DM5-HT; dimethylserotonin; N,N-dimethyl-5-HT; N,N-dimethylserotonin; 5-OH-DMT

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]

• Cross-matching ID:
  PubChem CID: 10257
  ChEBI ID: CHEBI:3210
  CAS Number: CAS 487-93-4
  TTD Drug ID: DMD1SY9

Molecule-Related Drug Atlas

Drug(s) Targeting 5-HT 1D receptor (HTR1D)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Metergolin	DMJFP6G	Hyperprolactinaemia	5A60.1	Approved	[7]
Eletriptan	DMW649X	Migraine	8A80	Approved	[8]
Zolmitriptan	DM1IB4Q	Migraine	8A80	Approved	[8]
Frovatriptan	DM7RE8P	Migraine	8A80	Approved	[8]
Sumatriptan	DMVYXR8	Cluster headache	8A81.0	Approved	[9]
Rizatriptan	DMDJMA3	Migraine	8A80	Approved	[10]
Almogran	DM7I64Z	Migraine	8A80	Approved	[11]
Neu-P11	DMIQDFW	Alzheimer disease	8A20	Phase 2	[12]
FKB01MD	DM2O7NM	N. A.	N. A.	Phase 2	[13]
NXN-188	DMMBAIH	Migraine	8A80	Phase 2	[14]

Drug(s) Targeting 5-HT 5A receptor (HTR5A)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Metergolin	DMJFP6G	Hyperprolactinaemia	5A60.1	Approved	[15]
(+/-)-nantenine	DM0L3GE	Discovery agent	N.A.	Investigative	[16]
SEROTONIN	DMOFCRY	Discovery agent	N.A.	Investigative	[17]
5-CT	DM260KD	Discovery agent	N.A.	Investigative	[4]
TFMPP	DMAC8TP	Discovery agent	N.A.	Investigative	[18]
5,6-dichloro-3,4-dihydroquinazolin-2-amine	DMN1S35	Discovery agent	N.A.	Investigative	[19]
MPDT	DMYX31S	Discovery agent	N.A.	Investigative	[20]
5-chloro-3,4-dihydroquinazolin-2-amine	DMKEFJ0	Discovery agent	N.A.	Investigative	[19]
EDMT	DMS3AXK	Discovery agent	N.A.	Investigative	[20]
5-chloro-4-methyl-3,4-dihydroquinazolin-2-amine	DM7FZU2	Discovery agent	N.A.	Investigative	[19]

Drug(s) Targeting 5-HT 6 receptor (HTR6)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
LU AE58054	DMWGRQD	Schizophrenia	6A20	Phase 3	[21]
SB-742457	DM6L4ZT	Alzheimer disease	8A20	Phase 3	[22]
AVN 211	DMVB4OS	Schizophrenia	6A20	Phase 2/3	[23]
SYN120	DMDF7XB	Parkinson disease	8A00.0	Phase 2	[24]
AVN 101	DMJFLBC	Alzheimer disease	8A20	Phase 2	[23]
SYN-120	DMPW0UL	Alzheimer disease	8A20	Phase 2	[25]
PF-05212377	DMPVQYR	Alzheimer disease	8A20	Phase 2	[26]
AVN 322	DMK2LGM	Cognitive impairment	6D71	Phase 2	[22]
SAM-531	DMHVJZ6	Alzheimer disease	8A20	Phase 2	[27]
SUVN-502	DMQD753	Alzheimer disease	8A20	Phase 2	[28]

Drug(s) Targeting 5-HT 2A receptor (HTR2A)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Metergolin	DMJFP6G	Hyperprolactinaemia	5A60.1	Approved	[29]
ZOTEPINE	DMF3VXA	Anxiety disorder	6B00-6B0Z	Approved	[30]
Iloperidone	DM6AUFY	Schizophrenia	6A20	Approved	[31]
Flibanserin	DM70DTN	Depression	6A70-6A7Z	Approved	[32]
Lurasidone hydrochloride	DMCVPXO	Schizophrenia	6A20	Approved	[33]
Aniracetam	DMOIFW0	Cerebrovascular ischaemia	8B1Z	Approved	[34]
lumateperone tosylate	DMQ8HOJ	Schizophrenia	6A20	Approved	[35]
Sarpogrelate	DMGLP6S	Diabetic complication	5A2Y	Approved	[36]
Pimavanserin	DMR7IVC	Parkinson disease	8A00.0	Approved	[37]
Zicronapine	DMP8ESD	Schizophrenia	6A20	Phase 3	[38]

Drug(s) Targeting 5-HT 7 receptor (HTR7)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
RP5063	DMKUE8O	Schizophrenia	6A20	Phase 2	[13]
JNJ-18038683	DMV1T59	Major depressive disorder	6A70.3	Phase 2	[39]
AVN-101	DMOGFNI	Cognitive impairment	6D71	Phase 2	[40]
ATI-9242	DM6GKMU	Schizophrenia	6A20	Phase 1	[41]
PMID30124346-Compound-34TABLE4	DM2G3VE	Attention deficit hyperactivity disorder	6A05.Z	Patented	[42]
PMID30124346-Compound-13TABLE4	DMHTJVA	Attention deficit hyperactivity disorder	6A05.Z	Patented	[42]
Carbamide derivative 2	DMW5GI3	N. A.	N. A.	Patented	[43]
4-oxadiazole derivative 1	DMWFHKR	N. A.	N. A.	Patented	[43]
SB-269970	DM8WTGA	Sleep-wake disorder	7A00-7B2Z	Terminated	[44]
4-(4-butylpiperidin-1-yl)-1-o-tolylbutan-1-one	DMM9X0G	Discovery agent	N.A.	Investigative	[45]

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
5-HT 1D receptor (HTR1D)	TT6MSOK	5HT1D_HUMAN	Antagonist	[2]
5-HT 2A receptor (HTR2A)	TTJQOD7	5HT2A_HUMAN	Antagonist	[3]
5-HT 5A receptor (HTR5A)	TTRUFDT	5HT5A_HUMAN	Antagonist	[4]
5-HT 6 receptor (HTR6)	TTJS8PY	5HT6R_HUMAN	Antagonist	[5]
5-HT 7 receptor (HTR7)	TTO9X1H	5HT7R_HUMAN	Agonist	[6]

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: 144).
• [2] Alniditan, a new 5-hydroxytryptamine1D agonist and migraine-abortive agent: ligand-binding properties of human 5-hydroxytryptamine1D alpha, human 5-hydroxytryptamine1D beta, and calf 5-hydroxytryptamine1D receptors investigated with [3H]5-hydroxytryptamine and [3H]alniditan. Mol Pharmacol. 1996 Dec;50(6):1567-80.
• [3] Mapping the binding site pocket of the serotonin 5-Hydroxytryptamine2A receptor. Ser3.36(159) provides a second interaction site for the protonated amine of serotonin but not of lysergic acid diethylamide or bufotenin. J Biol Chem. 1996 Jun 21;271(25):14672-5.
• [4] Expression of functional mouse 5-HT5A serotonin receptor in the methylotrophic yeast Pichia pastoris: pharmacological characterization and localization. FEBS Lett. 1995 Dec 27;377(3):451-6.
• [5] Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells. Neuropharmacology. 1997 Apr-May;36(4-5):713-20.
• [6] Molecular cloning of a mammalian serotonin receptor that activates adenylate cyclase. Mol Pharmacol. 1993 Aug;44(2):229-36.
• [7] Primary structure and functional characterization of a human 5-HT1D-type serotonin receptor. Mol Pharmacol. 1991 Aug;40(2):143-8.
• [8] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
• [9] Irritable bowel syndrome: new agents targeting serotonin receptor subtypes. Drugs. 2001;61(3):317-32.
• [10] An introduction to migraine: from ancient treatment to functional pharmacology and antimigraine therapy. Proc West Pharmacol Soc. 2002;45:199-210.
• [11] Efficacy and tolerability of subcutaneous almotriptan for the treatment of acute migraine: a randomized, double-blind, parallel-group, dose-finding study. Clin Ther. 2001 Nov;23(11):1867-75.
• [12] Clinical pipeline report, company report or official report of Neurim Pharmaceuticals.
• [13] Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
• [14] Company report (NeurAxon)
• [15] Cloning and characterisation of the human 5-HT5A serotonin receptor. FEBS Lett. 1994 Dec 5;355(3):242-6.
• [16] Synthetic studies and pharmacological evaluations on the MDMA ('Ecstasy') antagonist nantenine. Bioorg Med Chem Lett. 2010 Jan 15;20(2):628-31.
• [17] Identification of a potent, selective, and orally active leukotriene a4 hydrolase inhibitor with anti-inflammatory activity. J Med Chem. 2008 Jul 24;51(14):4150-69.
• [18] Mouse 5-hydroxytryptamine5A and 5-hydroxytryptamine5B receptors define a new family of serotonin receptors: cloning, functional expression, and chromosomal localization. Mol Pharmacol. 1993 Mar;43(3):313-9.
• [19] Cyclic guanidines as dual 5-HT5A/5-HT7 receptor ligands: structure-activity relationship elucidation. Bioorg Med Chem Lett. 2008 Jan 1;18(1):256-61.
• [20] 2-Substituted tryptamines: agents with selectivity for 5-HT(6) serotonin receptors. J Med Chem. 2000 Mar 9;43(5):1011-8.
• [21] Lu AE58054, a 5-HT6 antagonist, reverses cognitive impairment induced by subchronic phencyclidine in a novel object recognition test in rats. Int J Neuropsychopharmacol. 2010 Sep;13(8):1021-33.
• [22] 5-HT6 receptors and Alzheimer's disease. Alzheimers Res Ther. 2013; 5(2): 15.
• [23] Latrepirdine, a potential novel treatment for Alzheimer's disease and Huntington's chorea. Curr Opin Investig Drugs. 2010 January; 11(1): 80-91.
• [24] Therapeutic strategies for Parkinson disease: beyond dopaminergic drugs. Nat Rev Drug Discov. 2018 Nov;17(11):804-822.
• [25] The Serotonin-6 Receptor as a Novel Therapeutic Target. Exp Neurobiol. 2011 December; 20(4): 159-168.
• [26] PF-05212377 Alzheimer's Disease (Phase 2). Pfizer.
• [27] Activation of 5-HT6 receptors modulates sleep-wake activity and hippocampal theta oscillation. ACS Chem Neurosci. 2013 Jan 16;4(1):191-9.
• [28] Novel and Potent 5-Piperazinyl Methyl-N1-aryl Sulfonyl Indole Derivatives as 5-HT6 Receptor Ligands. ACS Med Chem Lett. 2010 October 14; 1(7): 340-344.
• [29] Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors. Naunyn Schmiedebergs Arch Pharmacol. 2004 Aug;370(2):114-23.
• [30] Current and novel approaches to the drug treatment of schizophrenia. J Med Chem. 2001 Feb 15;44(4):477-501.
• [31] Hughes B: 2009 FDA drug approvals. Nat Rev Drug Discov. 2010 Feb;9(2):89-92.
• [32] Radium 223 dichloride for prostate cancer treatment. Drug Des Devel Ther. 2017 Sep 6;11:2643-2651.
• [33] Mullard A: 2010 FDA drug approvals. Nat Rev Drug Discov. 2011 Feb;10(2):82-5.
• [34] Anxiolytic effects of aniracetam in three different mouse models of anxiety and the underlying mechanism. Eur J Pharmacol. 2001 May 18;420(1):33-43.
• [35] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2019
• [36] Beneficial effects of sarpogrelate hydrochloride, a 5-HT2A receptor antagonist, supplemented with pioglitazone on diabetic model mice. Endocr Res. 2009;34(1-2):18-30.
• [37] Pimavanserin, a selective serotonin (5-HT)2A-inverse agonist, enhances the efficacy and safety of risperidone, 2mg/day, but does not enhance efficacy of haloperidol, 2mg/day: comparison with reference dose risperidone, 6mg/day.Schizophr Res.2012 Nov;141(2-3):144-52.
• [38] Clinical pipeline report, company report or official report of Lundbeck.
• [39] Selective pharmacological blockade of the 5-HT7 receptor attenuates light and 8-OH-DPAT induced phase shifts of mouse circadian wheel running activity. Front Behav Neurosci. 2015 Jan 15;8:453.
• [40] AVN-101: A Multi-Target Drug Candidate for the Treatment of CNS Disorders. J Alzheimers Dis. 2016 May 25;53(2):583-620.
• [41] Pharmacological characteristics of ATI-9242, a Novel Atypical Antipsychotic. FASEB J, April, 2010, 24(Meeting Abstract Supplement),773.12.
• [42] 5-HT1A receptor ligands and their therapeutic applications: review of new patents.Expert Opin Ther Pat. 2018 Sep;28(9):679-689.
• [43] Acyltransferase inhibitors: a patent review (2010-present).Expert Opin Ther Pat. 2015 Feb;25(2):145-58.
• [44] [(3)H]-SB-269970--A selective antagonist radioligand for 5-HT(7) receptors. Br J Pharmacol. 2000 May;130(2):409-17.
• [45] Discovery of N-{1-[3-(3-oxo-2,3-dihydrobenzo[1,4]oxazin-4-yl)propyl]piperidin-4-yl}-2-phenylacetamide (Lu AE51090): an allosteric muscarinic M1 rec... J Med Chem. 2010 Sep 9;53(17):6386-97.