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 ;
CompTox Dashboard (EPA)	DTXSID8042632 ;
ECHA InfoCard	100.164.757
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 ;
	(what is this?) (verify)

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

^ Shearman GT, Tolcsvai L (1987). "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. doi:10.1007/bf00176488. PMID 3114804. S2CID 25814825.
^ Homesley HD, Hahne WF, McLees B, et al. (April 1993). "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. doi:10.1097/00000421-199304000-00020. PMID 8452114. S2CID 11733418.
^ McKinzie DL, McBride WJ, Murphy JM, Lumeng L, Li TK (October 2000). "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. doi:10.1111/j.1530-0277.2000.tb04567.x. PMID 11045857.
^ Kankaanpää A, Meririnne E, Seppälä T (February 2002). "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. doi:10.1007/s00213-001-0939-4. PMID 11823886. S2CID 21614467.
^ Kos T, Popik P, Pietraszek M, et al. (May 2006). "Effect of 5-HT3 receptor antagonist MDL 72222 on behaviors induced by ketamine in rats and mice". Eur Neuropsychopharmacol. 16 (4): 297–310. doi:10.1016/j.euroneuro.2005.10.001. PMID 16288851. S2CID 43575963.
^ Yoo JH, Nam YS, Lee SY, Jang CG (January 2008). "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. doi:10.1002/syn.20461. PMID 17948891. S2CID 20699645.

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[1] Shearman GT, Tolcsvai L (1987). "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. doi:10.1007/bf00176488. PMID 3114804. S2CID 25814825.

[2] Homesley HD, Hahne WF, McLees B, et al. (April 1993). "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. doi:10.1097/00000421-199304000-00020. PMID 8452114. S2CID 11733418.

[3] McKinzie DL, McBride WJ, Murphy JM, Lumeng L, Li TK (October 2000). "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. doi:10.1111/j.1530-0277.2000.tb04567.x. PMID 11045857.

[4] Kankaanpää A, Meririnne E, Seppälä T (February 2002). "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. doi:10.1007/s00213-001-0939-4. PMID 11823886. S2CID 21614467.

[5] Kos T, Popik P, Pietraszek M, et al. (May 2006). "Effect of 5-HT3 receptor antagonist MDL 72222 on behaviors induced by ketamine in rats and mice". Eur Neuropsychopharmacol. 16 (4): 297–310. doi:10.1016/j.euroneuro.2005.10.001. PMID 16288851. S2CID 43575963.

[6] Yoo JH, Nam YS, Lee SY, Jang CG (January 2008). "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. doi:10.1002/syn.20461. PMID 17948891. S2CID 20699645.

[1]

[2]

[3]

[4]

[5]

[6]

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
CompTox Dashboard (EPA)	DTXSID8042632
ECHA InfoCard	100.164.757
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
^NY (what is this?) (verify)

Bemesetron

See also

References