Altropane ATC code
Methyl (1R ,2S ,3S ,5S )-3-(4-fluorophenyl)-8-[(E )-3-iodoprop-2-enyl]-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Number PubChem CID ChemSpider UNII Formula C 18 H 21 F I N O 2 Molar mass 429.2694 g·mol−1 3D model (JSmol )
COC(=O)[C@@H]1[C@H]2CC[C@H](N2C\C=C\I)C[C@@H]1C3=CC=C(C=C3)F
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
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 125 I radiolabelled form for mapping the distribution of dopamine transporters in the brain,[1] Parkinson's disease .[2] 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 . ^ 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 .
Stimulants
Adamantanes
Adapromine Amantadine Bromantane Memantine Rimantadine Adenosine antagonists Alkylamines Ampakines Arylcyclohexylamines Benzazepines
6-Br-APB SKF-77434 SKF-81297 SKF-82958 Cathinones Cholinergics Convulsants Eugeroics Oxazolines Phenethylamines Phenylmorpholines Piperazines
2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 MeOPP MBZP oMPP Vanoxerine Piperidines Pyrrolidines Racetams
Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide Tropanes Tryptamines Others ATC code : N06B
Monoamine reuptake inhibitors
DAT (DRIs
Piperazines: DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 Nefazodone Vanoxerine
Pyrrolidines: Diphenylprolinol MDPV Naphyrone Prolintane Pyrovalerone
NET (NRIs
Norepinephrine–dopamine reuptake inhibitors: Amineptine Bupropion Fencamine Fencamfamin Hydroxybupropion Lefetamine Levophacetoperane LR-5182 Manifaxine Methylphenidate Nomifensine O-2172 Radafaxine Serdexmethylphenidate Solriamfetol
Tricyclic antidepressants: Amitriptyline Butriptyline Cianopramine Clomipramine Desipramine Dosulepin (dothiepin) Doxepin Imipramine Lofepramine Melitracen Nortriptyline Protriptyline Trimipramine
Tetracyclic antidepressants: Amoxapine Maprotiline Mianserin Oxaprotiline Setiptiline
Others: Antihistamines (e.g., brompheniramine , chlorphenamine , pheniramine , tripelennamine )Antipsychotics (e.g., loxapine , ziprasidone )Arylcyclohexylamines (e.g., ketamine , phencyclidine )Dopexamine Ephenidine Ginkgo biloba Indeloxazine Nefazodone Opioids (e.g., desmetramadol , methadone , pethidine (meperidine) , tapentadol , tramadol , levorphanol )
SERT (SRIs
Selective serotonin reuptake inhibitors and serotonin receptor modulators: Etoperidone Litoxetine Lubazodone LY-393558 Quipazine SB-649915 TGBA01AD Trazodone Vilazodone Vortioxetine
Tricyclic antidepressants: Amitriptyline Cianopramine Clomipramine Cyanodothiepin Desipramine Dosulepin (dothiepin) Doxepin Imipramine Lofepramine Nortriptyline Pipofezine Protriptyline
Others: Amoxapine Antihistamines (e.g., brompheniramine , chlorphenamine , dimenhydrinate , diphenhydramine , mepyramine (pyrilamine) , pheniramine , tripelennamine )Antipsychotics (e.g., loxapine , ziprasidone )Arylcyclohexylamines (e.g., 3-MeO-PCP , esketamine , ketamine , methoxetamine , phencyclidine )Cyclobenzaprine Delucemine Dextromethorphan Dextrorphan Efavirenz Hypidone Medifoxamine Mesembrine Mifepristone MIN-117 (WF-516) N-Me-5-HT Opioids (e.g., dextropropoxyphene , methadone , pethidine (meperidine) , levorphanol , tapentadol , tramadol )Roxindole
VMATs
Amiodarone Amphetamines (e.g., amphetamine , methamphetamine , MDMA )Bietaserpine Deserpidine Deutetrabenazine Dihydrotetrabenazine Efavirenz GBR-12935 Ibogaine Ketanserin Lobeline Reserpine Rose bengal Tetrabenazine Valbenazine Vanoxerine (GBR-12909) Others
DAT modulators: Agonist-like: SoRI-9804 ; Antagonist-like: SoRI-20041 See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
Phenyltropanes (classifications )
2-Carboxymethyl Esters (3,4-Disubstituted Phenyl)-tropanes
Dichloropane RTI-112 RTI-353 Arylcarboxy Carboxyalkyl Acyl β,α Stereochemistry α,β Stereochemistry Heterocycles: 3-Substituted-isoxazol-5-yl Heterocycles: 3-Substituted-1,2,4-oxadiazole N-alkyl N-replaced (S,O,C) Irreversible Nortropanes (N-demethylated)
