From Wikipedia, the free encyclopedia
Stimulant drug
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 | C18H21FINO2 |
---|
Molar mass | 429.274 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 YKey:GTQLIPQFXVKRKJ-UNSMHXHVSA-N Y
|
(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.
|
---|
DATTooltip Dopamine transporter (
DRIsTooltip Dopamine reuptake inhibitors) | |
---|
NETTooltip Norepinephrine transporter (
NRIsTooltip Norepinephrine reuptake inhibitors) | | | | | | |
- 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)
|
|
---|
SERTTooltip Serotonin transporter (
SRIsTooltip Serotonin reuptake inhibitors) | | | | |
- Others:
A-80426
-
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
|
|
---|
VMATsTooltip Vesicular monoamine transporters | |
---|
Others | |
---|
|
|
---|
2-Carboxymethyl Esters | |
---|
(3,4-Disubstituted Phenyl)-tropanes | |
---|
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) | |
---|