Altropane

Altropane
Clinical data
ATC code	none;
Identifiers
	IUPAC name Methyl (1R,2S,3S,5S)-3-(4-fluorophenyl)-8-[(E)-3-iodoprop-2-enyl]-8-azabicyclo[3.2.1]octane-2-carboxylate;
CAS Number	180468-34-2 ;
PubChem CID	6440180;
ChemSpider	4944487 ;
UNII	1Q4092099O;
CompTox Dashboard (EPA)	DTXSID901027571 ;
Chemical and physical data
Formula	C18H21FINO2
Molar mass	429.274 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC(=O)[C@@H]1[C@H]2CC[C@H](N2C\C=C\I)C[C@@H]1C3=CC=C(C=C3)F;
	InChI InChI=1S/C18H21FINO2/c1-23-18(22)17-15(12-3-5-13(19)6-4-12)11-14-7-8-16(17)21(14)10-2-9-20/h2-6,9,14-17H,7-8,10-11H2,1H3/b9-2+/t14-,15+,16+,17-/m0/s1 ; Key:GTQLIPQFXVKRKJ-UNSMHXHVSA-N ;
	(verify)

Altropane (O-587, IACFT, 2β-carbomethoxy-3β-(4-fluorophenyl)-N-((E)-3-iodo-prop-2-enyl)tropane) is a phenyltropane derivative which acts as a potent dopamine reuptake inhibitor and long-acting stimulant drug. It has mainly been used as the ¹²⁵I radiolabelled form for mapping the distribution of dopamine transporters in the brain,^[1] and consequently this has led to its development as a potential diagnostic tool for early detection of Parkinson's disease.^[2] It is also being investigated for potential use in the diagnosis and treatment of attention deficit hyperactivity disorder (ADHD).^[3]^[4]

References

^ Elmaleh DR, Fischman AJ, Shoup TM, Byon C, Hanson RN, Liang AY, et al. (July 1996). "Preparation and biological evaluation of iodine-125-IACFT: a selective SPECT agent for imaging dopamine transporter sites". Journal of Nuclear Medicine. 37 (7): 1197–202. PMID 8965198.
^ Fischman AJ, Bonab AA, Babich JW, Palmer EP, Alpert NM, Elmaleh DR, et al. (June 1998). "Rapid detection of Parkinson's disease by SPECT with altropane: a selective ligand for dopamine transporters". Synapse. 29 (2): 128–41. doi:10.1002/(SICI)1098-2396(199806)29:2<128::AID-SYN4>3.0.CO;2-9. PMID 9593103. S2CID 30543189.
^ Cattabeni F (November 2002). "Altropane (Boston Life Science)". Current Opinion in Investigational Drugs. 3 (11): 1647–51. PMID 12476968.
^ Spencer TJ, Biederman J, Madras BK, Dougherty DD, Bonab AA, Livni E, et al. (November 2007). "Further evidence of dopamine transporter dysregulation in ADHD: a controlled PET imaging study using altropane". Biological Psychiatry. 62 (9): 1059–61. doi:10.1016/j.biopsych.2006.12.008. PMC 2715944. PMID 17511972.

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[1] Elmaleh DR, Fischman AJ, Shoup TM, Byon C, Hanson RN, Liang AY, et al. (July 1996). "Preparation and biological evaluation of iodine-125-IACFT: a selective SPECT agent for imaging dopamine transporter sites". Journal of Nuclear Medicine. 37 (7): 1197–202. PMID 8965198.

[2] Fischman AJ, Bonab AA, Babich JW, Palmer EP, Alpert NM, Elmaleh DR, et al. (June 1998). "Rapid detection of Parkinson's disease by SPECT with altropane: a selective ligand for dopamine transporters". Synapse. 29 (2): 128–41. doi:10.1002/(SICI)1098-2396(199806)29:2<128::AID-SYN4>3.0.CO;2-9. PMID 9593103. S2CID 30543189.

[3] Cattabeni F (November 2002). "Altropane (Boston Life Science)". Current Opinion in Investigational Drugs. 3 (11): 1647–51. PMID 12476968.

[4] Spencer TJ, Biederman J, Madras BK, Dougherty DD, Bonab AA, Livni E, et al. (November 2007). "Further evidence of dopamine transporter dysregulation in ADHD: a controlled PET imaging study using altropane". Biological Psychiatry. 62 (9): 1059–61. doi:10.1016/j.biopsych.2006.12.008. PMC 2715944. PMID 17511972.

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Clinical data

ATC code	none
Identifiers
IUPAC name Methyl (1R,2S,3S,5S)-3-(4-fluorophenyl)-8-[(E)-3-iodoprop-2-enyl]-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Number	180468-34-2^Y
PubChem CID	6440180
ChemSpider	4944487^Y
UNII	1Q4092099O
CompTox Dashboard (EPA)	DTXSID901027571
Chemical and physical data
Formula	C₁₈H₂₁FINO₂
Molar mass	429.274 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COC(=O)[C@@H]1[C@H]2CC[C@H](N2C\C=C\I)C[C@@H]1C3=CC=C(C=C3)F
InChI InChI=1S/C18H21FINO2/c1-23-18(22)17-15(12-3-5-13(19)6-4-12)11-14-7-8-16(17)21(14)10-2-9-20/h2-6,9,14-17H,7-8,10-11H2,1H3/b9-2+/t14-,15+,16+,17-/m0/s1^Y Key:GTQLIPQFXVKRKJ-UNSMHXHVSA-N^Y
(verify)