MADAM

MADAM
Clinical data
Other names	N,N-Dimethyl-2-(2-amino-4-methylphenylthio)benzylamine
Drug class	Serotonin reuptake inhibitor
ATC code	None;
Identifiers
	IUPAC name 2-[2-[(dimethylamino)methyl]phenyl]sulfanyl-5-methylaniline;
PubChem CID	10084648;
ChEMBL	ChEMBL22183;
Chemical and physical data
Formula	C16H20N2S
Molar mass	272.41 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=CC(=C(C=C1)SC2=CC=CC=C2CN(C)C)N;
	InChI InChI=1S/C16H20N2S/c1-12-8-9-16(14(17)10-12)19-15-7-5-4-6-13(15)11-18(2)3/h4-10H,11,17H2,1-3H3; Key:UABIXNSHHIMZEP-UHFFFAOYSA-N;

MADAM, also known as N,N-dimethyl-2-(2-amino-4-methylphenylthio)benzylamine, is a highly potent and selective serotonin reuptake inhibitor (SRI) which is used in scientific research.^[1] Its affinity (K_d) for the serotonin transporter (SERT) is 60 pM (0.06 nM).^[1] Radiolabeled isotopologues of MADAM have been developed and used as radiotracers in positron emission tomography (PET) imaging.^[2]^[3]^[4]^[5] The drug was first described in the scientific literature by 2001.^[6]^[7]

References

^ ^a ^b Chalon S, Tarkiainen J, Garreau L, Hall H, Emond P, Vercouillie J, et al. (January 2003). "Pharmacological characterization of N,N-dimethyl-2-(2-amino-4-methylphenyl thio)benzylamine as a ligand of the serotonin transporter with high affinity and selectivity". The Journal of Pharmacology and Experimental Therapeutics. 304 (1): 81–87. doi:10.1124/jpet.102.042226. PMID 12490578.
^ Tarkiainen J, Vercouillie J, Emond P, Sandell J, hiltunen J, Frangin Y, et al. (2001). "Carbon-11 labelling of MADAM in two different positions: a highly selective PET radioligand for the serotonin transporter". Journal of Labelled Compounds and Radiopharmaceuticals. 44 (14): 1013–1023. doi:10.1002/jlcr.523. ISSN 0362-4803.
^ Larsen AK, Brennum LT, Egebjerg J, Sánchez C, Halldin C, Andersen PH (March 2004). "Selectivity of (3)H-MADAM binding to 5-hydroxytryptamine transporters in vitro and in vivo in mice; correlation with behavioural effects". British Journal of Pharmacology. 141 (6): 1015–1023. doi:10.1038/sj.bjp.0705693. PMC 1574267. PMID 14993096.
^ Halldin C, Lundberg J, Sóvágó J, Gulyás B, Guilloteau D, Vercouillie J, et al. (December 2005). "[(11)C]MADAM, a new serotonin transporter radioligand characterized in the monkey brain by PET". Synapse. 58 (3). New York, N.Y.: 173–183. doi:10.1002/syn.20189. PMID 16138320.
^ Lundberg J, Odano I, Olsson H, Halldin C, Farde L (September 2005). "Quantification of 11C-MADAM binding to the serotonin transporter in the human brain". Journal of Nuclear Medicine. 46 (9): 1505–1515. PMID 16157534.
^ Guilloteau D, Tarkiainen J, Garreau L, Vercouillie J, Emond P, Besnard JC, et al. (August 2001). "Pharmacological characterization of N, N-dimethyl-2 (2-amino-4-methylphenylthio) benzylamine or MADAM as a radioligand of the serotonin transporter with high affinity and selectivity". European Journal of Nuclear Medicine. 28 (8): 997.
^ Chalon S, Tarkiainen J, Garreau L, Hall H, Emond P, Vercouillie J, et al. (July 2002). "N,N-dimethyl-2-(2-amino-4-methylphenylthio) benzylamine or MADAM is a serotonin transporter ligand with high affinity and specificity: in vitro characterization". NeuroImage. 16 (3): S18.

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[ChalonTarkiainenGarreau2003-1] Chalon S, Tarkiainen J, Garreau L, Hall H, Emond P, Vercouillie J, et al. (January 2003). "Pharmacological characterization of N,N-dimethyl-2-(2-amino-4-methylphenyl thio)benzylamine as a ligand of the serotonin transporter with high affinity and selectivity". The Journal of Pharmacology and Experimental Therapeutics. 304 (1): 81–87. doi:10.1124/jpet.102.042226. PMID 12490578.

[TarkiainenVercouillieEmond2001-2] Tarkiainen J, Vercouillie J, Emond P, Sandell J, hiltunen J, Frangin Y, et al. (2001). "Carbon-11 labelling of MADAM in two different positions: a highly selective PET radioligand for the serotonin transporter". Journal of Labelled Compounds and Radiopharmaceuticals. 44 (14): 1013–1023. doi:10.1002/jlcr.523. ISSN 0362-4803.

[LarsenBrennumEgebjerg2004-3] Larsen AK, Brennum LT, Egebjerg J, Sánchez C, Halldin C, Andersen PH (March 2004). "Selectivity of (3)H-MADAM binding to 5-hydroxytryptamine transporters in vitro and in vivo in mice; correlation with behavioural effects". British Journal of Pharmacology. 141 (6): 1015–1023. doi:10.1038/sj.bjp.0705693. PMC 1574267. PMID 14993096.

[HalldinLundbergSóvágó2005-4] Halldin C, Lundberg J, Sóvágó J, Gulyás B, Guilloteau D, Vercouillie J, et al. (December 2005). "[(11)C]MADAM, a new serotonin transporter radioligand characterized in the monkey brain by PET". Synapse. 58 (3). New York, N.Y.: 173–183. doi:10.1002/syn.20189. PMID 16138320.

[LundbergOdanoOlsson2005-5] Lundberg J, Odano I, Olsson H, Halldin C, Farde L (September 2005). "Quantification of 11C-MADAM binding to the serotonin transporter in the human brain". Journal of Nuclear Medicine. 46 (9): 1505–1515. PMID 16157534.

[GuilloteauTarkiainenGarreau2001-6] Guilloteau D, Tarkiainen J, Garreau L, Vercouillie J, Emond P, Besnard JC, et al. (August 2001). "Pharmacological characterization of N, N-dimethyl-2 (2-amino-4-methylphenylthio) benzylamine or MADAM as a radioligand of the serotonin transporter with high affinity and selectivity". European Journal of Nuclear Medicine. 28 (8): 997.

[ChalonTarkiainenGarreau2002-7] Chalon S, Tarkiainen J, Garreau L, Hall H, Emond P, Vercouillie J, et al. (July 2002). "N,N-dimethyl-2-(2-amino-4-methylphenylthio) benzylamine or MADAM is a serotonin transporter ligand with high affinity and specificity: in vitro characterization". NeuroImage. 16 (3): S18.

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