DOV-102,677

DOV-102,677
Legal status
Legal status	US: Investigational New Drug;
Identifiers
	IUPAC name (1S,5R)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane;
CAS Number	410074-75-8 ;
PubChem CID	11637190;
ChemSpider	9811932 ;
UNII	NS8NWQ6NF4;
ChEMBL	ChEMBL488638 ;
CompTox Dashboard (EPA)	DTXSID50469820 ;
Chemical and physical data
Formula	C11H11Cl2N
Molar mass	228.12 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1[C@@H]2[C@]1(CNC2)C3=CC(=C(C=C3)Cl)Cl;
	InChI InChI=1S/C11H11Cl2N/c12-9-2-1-7(3-10(9)13)11-4-8(11)5-14-6-11/h1-3,8,14H,4-6H2/t8-,11+/m0/s1 ; Key:BSMNRYCSBFHEMQ-GZMMTYOYSA-N ;
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DOV-102,677 is a psychoactive drug being developed by Merck and is currently in clinical trials.^[1] It is a triple reuptake inhibitor (TRI), or serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI).^[1] It is the (−)-enantiomer of DOV-216,303, and its (+)-enantiomer is DOV-21,947 (amitifadine).

Instead of being developed for depression, DOV-102,677 is being developed for the treatment of alcoholism.^[2]

IC₅₀ values for the SERT, NET and DAT are 129 nM, 103 nM, and 133 nM.^[1]

Compound	Uptake			Binding
Compound	5-HT	NE	DA	SERT	NET	DAT
DOV-216,303	14	20	78	190	380	190
Amitifadine	12	23	96	100	260	210
DOV-102,677	130	100	130	740	1000	220

DOV-102,677 (20 mg/kg IP) increased extracellular levels of dopamine and serotonin in the prefrontal cortex to 320 and 280% above baseline 100 min after administration. Dopamine levels were stably increased for the duration (240 min) of the study, but serotonin levels declined to baseline by 200 min after administration. Norepinephrine levels increased linearly to a maximum of 348% at 240 min post-dosing.^[1]

References

^ ^a ^b ^c ^d Popik P, Krawczyk M, Golembiowska K, Nowak G, Janowsky A, Skolnick P, et al. (2006). "Pharmacological profile of the "triple" monoamine neurotransmitter uptake inhibitor, DOV 102,677". Cellular and Molecular Neurobiology. 26 (4–6): 857–73. doi:10.1007/s10571-006-9012-5. PMID 16636898. S2CID 34989472.
^ McMillen BA, Shank JE, Jordan KB, Williams HL, Basile AS (November 2007). "Effect of DOV 102,677 on the volitional consumption of ethanol by Myers' high ethanol-preferring rat". Alcoholism: Clinical and Experimental Research. 31 (11): 1866–71. doi:10.1111/j.1530-0277.2007.00513.x. PMID 17908267.

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[Popik-1] Popik P, Krawczyk M, Golembiowska K, Nowak G, Janowsky A, Skolnick P, et al. (2006). "Pharmacological profile of the "triple" monoamine neurotransmitter uptake inhibitor, DOV 102,677". Cellular and Molecular Neurobiology. 26 (4–6): 857–73. doi:10.1007/s10571-006-9012-5. PMID 16636898. S2CID 34989472.

[2] McMillen BA, Shank JE, Jordan KB, Williams HL, Basile AS (November 2007). "Effect of DOV 102,677 on the volitional consumption of ethanol by Myers' high ethanol-preferring rat". Alcoholism: Clinical and Experimental Research. 31 (11): 1866–71. doi:10.1111/j.1530-0277.2007.00513.x. PMID 17908267.

[1]

[2]

Legal status

Legal status	US: Investigational New Drug
Identifiers
IUPAC name (1S,5R)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane
CAS Number	410074-75-8^Y
PubChem CID	11637190
ChemSpider	9811932^N
UNII	NS8NWQ6NF4
ChEMBL	ChEMBL488638^N
CompTox Dashboard (EPA)	DTXSID50469820
Chemical and physical data
Formula	C₁₁H₁₁Cl₂N
Molar mass	228.12 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1[C@@H]2[C@]1(CNC2)C3=CC(=C(C=C3)Cl)Cl
InChI InChI=1S/C11H11Cl2N/c12-9-2-1-7(3-10(9)13)11-4-8(11)5-14-6-11/h1-3,8,14H,4-6H2/t8-,11+/m0/s1^N Key:BSMNRYCSBFHEMQ-GZMMTYOYSA-N^N
^NY (what is this?) (verify)