Chemistry:Bemesetron

Bemesetron
Clinical data
ATC code	none;
Identifiers
	IUPAC name [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3,5-dichlorobenzoate;
CAS Number	40796-97-2 ;
PubChem CID	671690;
ChemSpider	10498629 ;
UNII	O98T3677PA;
ChEMBL	ChEMBL2107804 ;
Chemical and physical data
Formula	C15H17Cl2NO2
Molar mass	314.21 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN3[C@@H]1CC[C@H]3C[C@H](C1)OC(=O)c2cc(Cl)cc(Cl)c2;
	InChI InChI=1S/C15H17Cl2NO2/c1-18-12-2-3-13(18)8-14(7-12)20-15(19)9-4-10(16)6-11(17)5-9/h4-6,12-14H,2-3,7-8H2,1H3/t12-,13+,14+ ; Key:MNJNPLVXBISNSX-WDNDVIMCSA-N ;
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Short description: Chemical compound

Bemesetron (MDL-72222) is a drug which acts as an antagonist at the 5HT₃ receptor.^[1] It has antiemetic effects comparable to metoclopramide,^[2] however it is not used clinically, instead its main application is in scientific research studying the involvement of the 5HT₃ receptor in the actions of drugs of abuse.^[3]^[4]^[5]^[6]

References

↑ "Effect of the selective 5-HT3 receptor antagonists ICS 205-930 and MDL 72222 on 5-HTP-induced head shaking and behavioral symptoms induced by 5-methoxy-N,N,dimethyltryptamine in rats: comparison with some other 5-HT receptor antagonists". Psychopharmacology 92 (4): 520–3. 1987. doi:10.1007/bf00176488. PMID 3114804.
↑ "Randomized comparison of the antiemetic efficacy of a serotonin type 3 receptor antagonist (MDL 72,222) with a high-dose metoclopramide regimen". Am. J. Clin. Oncol. 16 (2): 175–9. April 1993. doi:10.1097/00000421-199304000-00020. PMID 8452114.
↑ "Effects of MDL 72222, a serotonin3 antagonist, on operant responding for ethanol by alcohol-preferring P rats". Alcohol. Clin. Exp. Res. 24 (10): 1500–4. October 2000. doi:10.1111/j.1530-0277.2000.tb04567.x. PMID 11045857.
↑ "5-HT3 receptor antagonist MDL 72222 attenuates cocaine- and mazindol-, but not methylphenidate-induced neurochemical and behavioral effects in the rat". Psychopharmacology 159 (4): 341–50. February 2002. doi:10.1007/s00213-001-0939-4. PMID 11823886.
↑ "Effect of 5-HT3 receptor antagonist MDL 72222 on behaviors induced by ketamine in rats and mice". Eur Neuropsychopharmacol 16 (4): 297–310. May 2006. doi:10.1016/j.euroneuro.2005.10.001. PMID 16288851.
↑ "Dopamine neurotransmission is involved in the attenuating effects of 5-HT3 receptor antagonist MDL 72222 on acute methamphetamine-induced locomotor hyperactivity in mice". Synapse 62 (1): 8–13. January 2008. doi:10.1002/syn.20461. PMID 17948891.

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Original source: https://en.wikipedia.org/wiki/Bemesetron. Read more

[1] "Effect of the selective 5-HT3 receptor antagonists ICS 205-930 and MDL 72222 on 5-HTP-induced head shaking and behavioral symptoms induced by 5-methoxy-N,N,dimethyltryptamine in rats: comparison with some other 5-HT receptor antagonists". Psychopharmacology 92 (4): 520–3. 1987. doi:10.1007/bf00176488. PMID 3114804.

[2] "Randomized comparison of the antiemetic efficacy of a serotonin type 3 receptor antagonist (MDL 72,222) with a high-dose metoclopramide regimen". Am. J. Clin. Oncol. 16 (2): 175–9. April 1993. doi:10.1097/00000421-199304000-00020. PMID 8452114.

[3] "Effects of MDL 72222, a serotonin3 antagonist, on operant responding for ethanol by alcohol-preferring P rats". Alcohol. Clin. Exp. Res. 24 (10): 1500–4. October 2000. doi:10.1111/j.1530-0277.2000.tb04567.x. PMID 11045857.

[4] "5-HT3 receptor antagonist MDL 72222 attenuates cocaine- and mazindol-, but not methylphenidate-induced neurochemical and behavioral effects in the rat". Psychopharmacology 159 (4): 341–50. February 2002. doi:10.1007/s00213-001-0939-4. PMID 11823886.

[5] "Effect of 5-HT3 receptor antagonist MDL 72222 on behaviors induced by ketamine in rats and mice". Eur Neuropsychopharmacol 16 (4): 297–310. May 2006. doi:10.1016/j.euroneuro.2005.10.001. PMID 16288851.

[6] "Dopamine neurotransmission is involved in the attenuating effects of 5-HT3 receptor antagonist MDL 72222 on acute methamphetamine-induced locomotor hyperactivity in mice". Synapse 62 (1): 8–13. January 2008. doi:10.1002/syn.20461. PMID 17948891.

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v t e Treatment of drug dependence (N07B)
Nicotine dependence	Bupropion Cytisine Lobeline Mecamylamine Varenicline AA (Clonidine)
Alcohol dependence	AD inhibitor (Disulfiram Calcium carbimide Hydrogen cyanamide) Acamprosate Opioid antagonists Naltrexone Nalmefene) κ-Opioid receptor antagonists Aticaprant Topiramate AA (Clonidine) Baclofen Metadoxine Phenibut
Opioid dependence	AA (Clonidine Lofexidine) Ibogaine Opioids Buprenorphine (+naloxone) Levacetylmethadol Methadone Dihydrocodeine Dihydroetorphine Hydromorphone (extended-release) Morphine (extended-release) Opioid antagonists (Naltrexone Nalmefene)
Benzodiazepine dependence	AA (Clonidine) Benzodiazepines (Diazepam Lorazepam Chlordiazepoxide Oxazepam) Barbiturates (Phenobarbital)
Research	Salvia divinorum

v t e Antiemetics (A04)
5-HT₃ serotonin ion channel antagonists	Alosetron Azasetron Bemesetron Cilansetron Clozapine Dazopride Dolasetron Granisetron Lerisetron Metoclopramide Mianserin Mirtazapine Olanzapine Ondansetron Palonosetron (+netupitant) Quetiapine Ramosetron Ricasetron Tropisetron Zatosetron
5-HT serotonin G-protein receptor antagonists	Clozapine Cyproheptadine Hydroxyzine Olanzapine Risperidone Ziprasidone
CB₁ agonists (cannabinoids)	Dronabinol Nabilone Tetrahydrocannabinol (cannabis)
D₂/D₃ antagonists	Alizapride Bromopride Chlorpromazine Clebopride Domperidone Haloperidol Hydroxyzine Itopride Metoclopramide Metopimazine Prochlorperazine Thiethylperazine Trimethobenzamide
H₁ antagonists (antihistamines)	Cyclizine Dimenhydrinate Diphenhydramine Hydroxyzine Meclizine Promethazine
mACh antagonists (anticholinergics)	Atropine Diphenhydramine Hydroxyzine (very mild) Hyoscyamine Scopolamine
NK₁ antagonists	Aprepitant Casopitant Ezlopitant Fosaprepitant Maropitant Netupitant Rolapitant Vestipitant
Others	Cerium oxalate Dexamethasone Lorazepam Midazolam Propofol

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Clinical data

ATC code	none
Identifiers
IUPAC name [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3,5-dichlorobenzoate
CAS Number	40796-97-2^N
PubChem CID	671690
ChemSpider	10498629^Y
UNII	O98T3677PA
ChEMBL	ChEMBL2107804^N
Chemical and physical data
Formula	C₁₅H₁₇Cl₂NO₂
Molar mass	314.21 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN3[C@@H]1CC[C@H]3C[C@H](C1)OC(=O)c2cc(Cl)cc(Cl)c2
InChI InChI=1S/C15H17Cl2NO2/c1-18-12-2-3-13(18)8-14(7-12)20-15(19)9-4-10(16)6-11(17)5-9/h4-6,12-14H,2-3,7-8H2,1H3/t12-,13+,14+^Y Key:MNJNPLVXBISNSX-WDNDVIMCSA-N^Y
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