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(-)-Vesamicol

HCID 659840
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
112709-59-8
Standard SMILES
O[C@@H]1CCCC[C@H]1N1CCC(c2ccccc2)CC1
InChIKey
YSSBJODGIYRAMI-IAGOWNOFSA-N
Molecular formula
C17H25NO
Average molar mass
259.4 g/mol
Monoisotopic mass
259.19361442

Overview

(1R,2R)-2-(4-phenyl-1-piperidinyl)-1-cyclohexanol is a member of piperidines.

Names & identifiers

Preferred name
(-)-Vesamicol
IUPAC
trans-(1R,2R)-2-(4-phenylpiperidin-1-yl)cyclohexan-1-ol
English name
L-(-)-VESAMICOL HYDROCHLORIDE
Molecular formula
C17H25NO
Molecular weight
259.39

Names & synonyms

(-)-Vesamicol112709-59-8(1R,2R)-2-(4-phenylpiperidin-1-yl)cyclohexan-1-ol115362-28-2Vesamicol, (+/-)-(1R,2R)-2-(4-Phenyl-1-piperidinyl)cyclohexanolCHEMBL207303D416V0FLMI1A877466VL-(-)-Vesamicol hydrochloride(+-)Vesamicolrel-(1R,2R)-2-(4-Phenylpiperidin-1-yl)cyclohexan-1-ol
Show more names
L(-)-VESAMICOL HCL1r-trans-cyclohexano(-)-Vesamicol (AH5183)Cyclohexanol, 2-(4-phenyl-1-piperidinyl)-, (1R,2R)-L-(-)-2-(4-Phenylpiperidino)cyclohexanol hydrochloride
Vesamicol, (-)-UNII-3D416V0FLMUNII-I1A877466VCyclohexanol, 2-(4-phenyl-1-piperidinyl)-, 1R-trans-Cyclohexanol, 2-(4-phenyl-1-piperidinyl)-, trans(+-)-J404.506HPrestwick3_000920L-(-)-VESAMICOL

Database identifiers

CAS
112709-59-8、115362-28-2
PubChem CID
659840
DTXSID
DTXSID20920872

Properties

Computed structural properties

XLogP
3.2
Topological polar surface area
23.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
19
Formal charge
0
Complexity
266

Physicochemical properties

Melting point
238.5 · 238.5-240.0 °C
Boiling point
393.5 · 393.5±42.0 °C(Predicted)
Density
1.086 · 1.086±0.06 g/cm3(Predicted)
pka
15.16 · 15.16±0.40(Predicted)
form
solid
color
white
FDA UNII
1 A877466V · I1A877466V
Safety Statements
22 · 22-24/25
WGK Germany
3 · 3
RTECS
765050 · GW0765050

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety & protection

Minimum Risk LevelAcute Oral: 0.01 mg/kg/day (L134) Intermediate Oral: 0.01 mg/kg/day (L134)

Toxicology

Health Effects · 1 item

People must absorb small amounts of copper every day because copper is essential for good health, however, high levels of copper can be harmful. Very-high doses of copper can cause damage to your liver and kidneys, and can even cause death. Copper may induce allergic responses in sensitive individuals. (L278, L279)

Exposure RoutesOral (L277) ; inhalation (L277) ; dermal (L277)
Toxicity Summary · 1 item

Excess copper is sequestered within hepatocyte lysosomes, where it is complexed with metallothionein. Copper hepatotoxicity is believed to occur when the lysosomes become saturated and copper accumulates in the nucleus, causing nuclear damage. This damage is possibly a result of oxidative damage, including lipid peroxidation. Copper inhibits the sulfhydryl group enzymes such as glucose-6-phosphate 1-dehydrogenase, glutathione reductase, and paraoxonases, which protect the cell from free oxygen radicals. It also influences gene expression and is a co-factor for oxidative enzymes such as cytochrome C oxidase and lysyl oxidase. In addition, the oxidative stress induced by copper is thought to activate acid sphingomyelinase, which lead to the production of ceramide, an apoptotic signal, as well as cause hemolytic anemia. Copper-induced emesis results from stimulation of the vagus nerve. (L277, T49, A174, L280)

Signs and SymptomsBreathing high levels of copper can cause irritation of the nose and throat. Ingesting high levels of copper can cause nausea, vomiting, diarrhea, headache, dizziness, and respiratory difficulty. (L278, L279)
Carcinogen Classification

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Copper is mainly absorbed through the gastrointestinal tract, but it can also be inhalated and absorbed dermally. It passes through the basolateral membrane, possibly via regulatory copper transporters, and is transported to the liver and kidney bound to serum albumin. The liver is the critical organ for copper homoeostasis. In the liver and other tissues, copper is stored bound to metallothionein, amino acids, and in association with copper-dependent enzymes, then partitioned for excretion through the bile or incorporation into intra- and extracellular proteins. The transport of copper to the peripheral tissues is accomplished through the plasma attached to serum albumin, ceruloplasmin or low-molecular-weight complexes. Copper may induce the production of metallothionein and ceruloplasmin. The membrane-bound copper transporting adenosine triphosphatase (Cu-ATPase) transports copper ions into and out of cells. Physiologically normal levels of copper in the body are held constant by alterations in the rate and amount of copper absorption, compartmental distribution, and excretion. (L277, L279)

Applications

Uses(-)-Vesamicol (AH5183) is an inhibitor of acetylcholine transport into synaptic vesicles, with the IC50 of 75 nM[1]. (-)-Vesamicol can be used for release and recycling of synaptic vesicles study[1].

Suppliers4 total

武汉易泰科技有限公司上海分公司18930552037 · [email protected]
上海阿拉丁生化科技股份有限公司6206333 13167063860 · [email protected]
南通全益生物科技有限公司+86-0513; 18051384581 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]

Additional notes

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
ChEMBL
CHEMBL20730
ChEBI
CHEBI:92261
UNII
3D416V0FLM、I1A877466V
Nikkaji
J404.506H
No indication of carcinogenicity to humans (not listed by IARC).

Safety data

wgk
3
rtecs
GW0765050
safety_code
22-24/25

DefinitionChEBI: (1R,2R)-2-(4-phenyl-1-piperidinyl)-1-cyclohexanol is a member of piperidines.