L-741 626

L-741,626
Clinical data
ATC code	none;
Identifiers
	IUPAC name 3-[4-(4-Chlorophenyl)-4-hydroxypiperidin-l-yl]methyl-1H-indole;
CAS Number	81226-60-0 ;
PubChem CID	133633;
IUPHAR/BPS	177;
ChemSpider	117877 ;
UNII	WTW4A6SW92;
CompTox Dashboard ( EPA)	DTXSID30230974 ;
Chemical and physical data
Formula	C20H21ClN2O
Molar mass	340.85 g·mol−1
3D model ( JSmol)	Interactive image;
	SMILES OC(CC1)(C2=CC=C(Cl)C=C2)CCN1CC3=CNC4=CC=CC=C43;
	InChI InChI=1S/C20H21ClN2O/c21-17-7-5-16(6-8-17)20(24)9-11-23(12-10-20)14-15-13-22-19-4-2-1-3-18(15)19/h1-8,13,22,24H,9-12,14H2 ; Key:LLBLNMUONVVVPG-UHFFFAOYSA-N ;
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L-741,626 is a drug which acts as a potent and selective antagonist for the dopamine receptor D₂. It has good selectivity over the related D₃ and D₄ subtypes and other receptors. L-741,626 is used for laboratory research into brain function and has proved particularly useful for distinguishing D₂ mediated responses from those produced by the closely related D₃ subtype, and for studying the roles of these subtypes in the action of cocaine and amphetamines in the brain.^[1]^[2]^[3]^[4]^[5]^[6]^[7]^[8]^[9]^[10]

References

^ Bowery BJ, Razzaque Z, Emms F, Patel S, Freedman S, Bristow L, Kulagowski J, Seabrook GR (December 1996). "Antagonism of the effects of (+)-PD 128907 on midbrain dopamine neurones in rat brain slices by a selective D2 receptor antagonist L-741,626". British Journal of Pharmacology. 119 (7): 1491–7. doi: 10.1111/j.1476-5381.1996.tb16063.x. PMC 1915834. PMID 8968560.
^ Canales JJ, Iversen SD (September 2000). "Psychomotor-activating effects mediated by dopamine D(2) and D(3) receptors in the nucleus accumbens". Pharmacology Biochemistry and Behavior. 67 (1): 161–8. doi: 10.1016/S0091-3057(00)00311-7. PMID 11113496. S2CID 26640822.
^ Costanza RM, Barber DJ, Terry P (November 2001). "Antagonism of the discriminative stimulus effects of cocaine at two training doses by dopamine D2-like receptor antagonists". Psychopharmacology. 158 (2): 146–53. doi: 10.1007/s002130100872. PMID 11702088. S2CID 22530289.
^ Chaperon F, Tricklebank MD, Unger L, Neijt HC (June 2003). "Evidence for regulation of body temperature in rats by dopamine D2 receptor and possible influence of D1 but not D3 and D4 receptors". Neuropharmacology. 44 (8): 1047–53. doi: 10.1016/S0028-3908(03)00113-8. PMID 12763098. S2CID 19219652.
^ Grundt P, Husband SL, Luedtke RR, Taylor M, Newman AH (February 2007). "Analogues of the dopamine D2 receptor antagonist L741,626: Binding, function, and SAR". Bioorganic & Medicinal Chemistry Letters. 17 (3): 745–9. doi: 10.1016/j.bmcl.2006.10.076. PMC 1851912. PMID 17095222.
^ Koffarnus MN, Greedy B, Husbands SM, Grundt P, Newman AH, Woods JH (April 2009). "The discriminative stimulus effects of dopamine D2- and D3-preferring agonists in rats". Psychopharmacology. 203 (2): 317–27. doi: 10.1007/s00213-008-1323-4. PMC 3065021. PMID 18807248.
^ Depoortère R, Bardin L, Rodrigues M, Abrial E, Aliaga M, Newman-Tancredi A (July 2009). "Penile erection and yawning induced by dopamine D2-like receptor agonists in rats: influence of strain and contribution of dopamine D2, but not D3 and D4 receptors". Behavioural Pharmacology. 20 (4): 303–11. doi: 10.1097/FBP.0b013e32832ec5aa. PMID 19584712. S2CID 35558814.
^ Fan X, Xu M, Hess EJ (January 2010). "D2 dopamine receptor subtype-mediated hyperactivity and amphetamine responses in a model of ADHD". Neurobiology of Disease. 37 (1): 228–36. doi: 10.1016/j.nbd.2009.10.009. PMC 2839459. PMID 19840852.
^ Achat-Mendes C, Grundt P, Cao J, Platt DM, Newman AH, Spealman RD (August 2010). "Dopamine D3 and D2 receptor mechanisms in the abuse-related behavioral effects of cocaine: studies with preferential antagonists in squirrel monkeys". The Journal of Pharmacology and Experimental Therapeutics. 334 (2): 556–65. doi: 10.1124/jpet.110.167619. PMC 2913766. PMID 20494958.
^ Watson DJ, Marsden CA, Millan MJ, Fone KC (March 2011). "Blockade of dopamine D3 but not D2 receptors reverses the novel object discrimination impairment produced by post-weaning social isolation: implications for schizophrenia and its treatment". The International Journal of Neuropsychopharmacology. 15 (4): 471–484. doi: 10.1017/S1461145711000435. PMID 21414250.

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[pmid8968560-1] Bowery BJ, Razzaque Z, Emms F, Patel S, Freedman S, Bristow L, Kulagowski J, Seabrook GR (December 1996). "Antagonism of the effects of (+)-PD 128907 on midbrain dopamine neurones in rat brain slices by a selective D2 receptor antagonist L-741,626". British Journal of Pharmacology. 119 (7): 1491–7. doi: 10.1111/j.1476-5381.1996.tb16063.x. PMC 1915834. PMID 8968560.

[pmid11113496-2] Canales JJ, Iversen SD (September 2000). "Psychomotor-activating effects mediated by dopamine D(2) and D(3) receptors in the nucleus accumbens". Pharmacology Biochemistry and Behavior. 67 (1): 161–8. doi: 10.1016/S0091-3057(00)00311-7. PMID 11113496. S2CID 26640822.

[pmid11702088-3] Costanza RM, Barber DJ, Terry P (November 2001). "Antagonism of the discriminative stimulus effects of cocaine at two training doses by dopamine D2-like receptor antagonists". Psychopharmacology. 158 (2): 146–53. doi: 10.1007/s002130100872. PMID 11702088. S2CID 22530289.

[pmid12763098-4] Chaperon F, Tricklebank MD, Unger L, Neijt HC (June 2003). "Evidence for regulation of body temperature in rats by dopamine D2 receptor and possible influence of D1 but not D3 and D4 receptors". Neuropharmacology. 44 (8): 1047–53. doi: 10.1016/S0028-3908(03)00113-8. PMID 12763098. S2CID 19219652.

[pmid17095222-5] Grundt P, Husband SL, Luedtke RR, Taylor M, Newman AH (February 2007). "Analogues of the dopamine D2 receptor antagonist L741,626: Binding, function, and SAR". Bioorganic & Medicinal Chemistry Letters. 17 (3): 745–9. doi: 10.1016/j.bmcl.2006.10.076. PMC 1851912. PMID 17095222.

[pmid18807248-6] Koffarnus MN, Greedy B, Husbands SM, Grundt P, Newman AH, Woods JH (April 2009). "The discriminative stimulus effects of dopamine D2- and D3-preferring agonists in rats". Psychopharmacology. 203 (2): 317–27. doi: 10.1007/s00213-008-1323-4. PMC 3065021. PMID 18807248.

[pmid19584712-7] Depoortère R, Bardin L, Rodrigues M, Abrial E, Aliaga M, Newman-Tancredi A (July 2009). "Penile erection and yawning induced by dopamine D2-like receptor agonists in rats: influence of strain and contribution of dopamine D2, but not D3 and D4 receptors". Behavioural Pharmacology. 20 (4): 303–11. doi: 10.1097/FBP.0b013e32832ec5aa. PMID 19584712. S2CID 35558814.

[pmid19840852-8] Fan X, Xu M, Hess EJ (January 2010). "D2 dopamine receptor subtype-mediated hyperactivity and amphetamine responses in a model of ADHD". Neurobiology of Disease. 37 (1): 228–36. doi: 10.1016/j.nbd.2009.10.009. PMC 2839459. PMID 19840852.

[pmid20494958-9] Achat-Mendes C, Grundt P, Cao J, Platt DM, Newman AH, Spealman RD (August 2010). "Dopamine D3 and D2 receptor mechanisms in the abuse-related behavioral effects of cocaine: studies with preferential antagonists in squirrel monkeys". The Journal of Pharmacology and Experimental Therapeutics. 334 (2): 556–65. doi: 10.1124/jpet.110.167619. PMC 2913766. PMID 20494958.

[pmid21414250-10] Watson DJ, Marsden CA, Millan MJ, Fone KC (March 2011). "Blockade of dopamine D3 but not D2 receptors reverses the novel object discrimination impairment produced by post-weaning social isolation: implications for schizophrenia and its treatment". The International Journal of Neuropsychopharmacology. 15 (4): 471–484. doi: 10.1017/S1461145711000435. PMID 21414250.

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References

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Clinical data

ATC code	none
Identifiers
IUPAC name 3-[4-(4-Chlorophenyl)-4-hydroxypiperidin-l-yl]methyl-1H-indole
CAS Number	81226-60-0^Y
PubChem CID	133633
IUPHAR/BPS	177
ChemSpider	117877^N
UNII	WTW4A6SW92
CompTox Dashboard ( EPA)	DTXSID30230974
Chemical and physical data
Formula	C₂₀H₂₁ClN₂O
Molar mass	340.85 g·mol⁻¹
3D model ( JSmol)	Interactive image
SMILES OC(CC1)(C2=CC=C(Cl)C=C2)CCN1CC3=CNC4=CC=CC=C43
InChI InChI=1S/C20H21ClN2O/c21-17-7-5-16(6-8-17)20(24)9-11-23(12-10-20)14-15-13-22-19-4-2-1-3-18(15)19/h1-8,13,22,24H,9-12,14H2^N Key:LLBLNMUONVVVPG-UHFFFAOYSA-N^N
^NY (what is this?) (verify)