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3-(1-Methylpyrrolidin-2-yl)pyridine

HCID 942
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Grundinformationen

CAS
22083-74-5
Standard-SMILES
CN1CCCC1c1cccnc1
InChIKey
SNICXCGAKADSCV-UHFFFAOYSA-N
Summenformel
C10H14N2
Durchschnittliche Molmasse
162,23 g/mol
Monoisotopische Masse
162,11569846

Überblick

3-(1-methylpyrrolidin-2-yl)pyridine is an N-alkylpyrrolidine that consists of N-methylpyrrolidine bearing a pyridin-3-yl substituent at position 2. It is a pyridine alkaloid, a pyrrolidine alkaloid and a N-alkylpyrrolidine.

Namen und Bezeichner

Bevorzugter Name
3-(1-Methylpyrrolidin-2-yl)pyridine
IUPAC
3-(1-methylpyrrolidin-2-yl)pyridine

Namen und Synonyme

3-(1-methylpyrrolidin-2-yl)pyridineDL-NicotineDTXSID3048154CHEBI:1380003-[1-Methylpyrrolidin-2-yl]pyridineRefChem:489602(+-)NICOTINEDTXCID9028128623-834-222083-74-5(+/-)-Nicotine(R,S)-Nicotine
Weitere Namen anzeigen
rac-Nicotine(RS)-Nicotine(+-)-Nicotine75202-10-7CHEMBL440464S-(-)-Nicotinedestruxolfumeto bac

Datenbank-Bezeichner

CAS
22083-74-5、54-11-5
PubChem CID
942
DTXSID
DTXSID3048154
ChEMBL
CHEMBL440464
ChEBI
CHEBI:138000
EC Number
623-834-2
Nikkaji
J23.948H

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,2
Polarare Oberfläche (TPSA)
16,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
1
Schwere Atome
12
Formalladung
0
Komplexität
147

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H301 (92.7%): Toxic if swallowed [Danger Acute toxicity, oral]

P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 3 (92.7%)

Toxikologische Informationen

Treatment · 1 Eintrag

Other supportive measures include diazepam or barbiturates for seizures, atropine for excessive bronchial secretions or diarrhea, respiratory support for respiratory failure, and vigorous fluid support for hypotension and cardiovascular collapse. (L1712)

Health EffectsNicotine has mood-altering effects that may include relaxation, sharpness, calmness, and alertness. It may act as a stimulant or sedative/pain killer, depending on the dosage. (L327)
Exposure Routes · 1 Eintrag

Oral (L327) ; Inhalation (L327) Absorption of nicotine through the buccal mucosa is relatively slow and the high and rapid rise followed by the decline in nicotine arterial plasma concentrations seen with cigarette smoking are not achieved with the inhaler. About 10% of absorbed nicotine is excreted unchanged in urine.

Toxicity Summary · 1 Eintrag

Nicotine is a stimulant drug that acts as an agonist at nicotinic acetylcholine receptors. These are ionotropic receptors composed up of five homomeric or heteromeric subunits. In the brain, nicotine binds to nicotinic acetylcholine receptors on dopaminergic neurons in the cortico-limbic pathways. This causes the channel to open and allow conductance of multiple cations including sodium, calcium, and potassium. This leads to depolarization, which activates voltage-gated calcium channels and allows more calcium to enter the axon terminal. Calcium stimulates vesicle trafficking towards the plasma membrane and the release of dopamine into the synapse. Dopamine binding to its receptors is responsible the euphoric and addictive properties of nicotine. Nicotine also binds to nicotinic acetylcholine receptors on the chromaffin cells in the adrenal medulla. Binding opens the ion channel allowing influx of sodium, causing depolarization of the cell, which activates voltage-gated calcium channels. Calcium triggers the release of epinephrine from intracellular vesicles into the bloodstream, which causes vasoconstriction, increased blood pressure, increased heart rate, and increased blood sugar.

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

Nicotine has known human metabolites that include Nicotine N-glucuronide.

As nicotine enters the body, it is distributed quickly through the bloodstream and can cross the blood-brain barrier. On average it takes about seven seconds for the substance to reach the brain when inhaled. The half life of nicotine in the body is around two hours. Nicotine is metabolized in the liver by cytochrome P450 enzymes (mostly CYP2A6, and also by CYP2B6). A major metabolite is cotinine. Other primary metabolites include nicotine N'-oxide, nornicotine, nicotine isomethonium ion, 2-hydroxynicotine and nicotine glucuronide. (L327) Route of Elimination: About 10% of the nicotine absorbed is excreted unchanged in the urine. Half Life: Cotinine has a half life of 15-20 hours, while nicotine has a half life of 1-3 hours

Verwendung und Herstellung

Uses · 1 Eintrag

Nicotine is highly toxic alkaloid found in the nightshade family of plants (Solanaceae). (L327) NICOTROL Inhaler is indicated as an aid to smoking cessation for the relief of nicotine withdrawal symptoms. NICOTROL Inhaler therapy is recommended for use as part of a comprehensive behavioral smoking cessation program. It is used for the relief of nicotine withdrawal symptoms and as an aid to smoking cessation.

Zugehörige Reaktionen

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HRID 11750als Eduktuspto-grants-2006_08
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HRID 44666als Eduktuspto-grants-2013_09
Reaktionsgleichung von HRID 55545
HRID 55545als Eduktuspto-grants-1997_04
Reaktionsgleichung von HRID 59711
HRID 59711als Produktuspto-grants-2016_09
Reaktionsgleichung von HRID 175040
HRID 175040als ProduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Reaktionsgleichung von HRID 218056
HRID 218056als Eduktuspto-grants-2012_06
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Signs and SymptomsSymptoms of overdose include nausea, abdominal pain, vomiting, diarrhea, diaphoresis, flushing, dizziness, disturbed hearing and vision, confusion, weakness, palpitations, altered respiration and hypotension.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataLD50: 140 mg/kg (Dermal, Rat) LD50: 25 mg/kg (Subcutaneous, Rat) LD50: 5900 ug/kg (Intraperitoneal, Mouse) LD50: 2.8 mg/kg (Intravenous, Rat) (T80) LD50: 24 mg/kg (Oral, Mouse) (T18)