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Phenmetrazine Hydrochloride

HCID 92159
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
1707-14-8
Standard SMILES
CC1NCCOC1c1ccccc1.Cl
InChIKey
VJNXVAVKCZJOFQ-UHFFFAOYSA-N
Molecular formula
C11H16ClNO
Average molar mass
213.7 g/mol
Monoisotopic mass
213.0920418

Overview

Phenmetrazine hydrochloride is an organic molecular entity.

Names & identifiers

Preferred name
Phenmetrazine Hydrochloride
IUPAC
3-methyl-2-phenylmorpholine;hydrochloride

Names & synonyms

Phenmetrazine hydrochloridePreludin1707-14-83-Methyl-2-phenylmorpholine hydrochlorideUSAF GE-1Morpholine, 3-methyl-2-phenyl-, hydrochloridePhenmetrazine HClDTXSID0047822NSC-405728DTXCID8027799Phenmetrazine hydrochloride (USP)Phenmetrazine hydrochloride [USP]
Show more names
Phenmetrazine chlorideRefChem:57629Hydrochloride, Phenmetrazine3-methyl-2-phenyl-morpholine;hydrochloride216-950-66U85YRT588MefolinMarsin

Database identifiers

CAS
1707-14-8
PubChem CID
92159
DTXSID
DTXSID0047822
ChEMBL
CHEMBL1200483
ChEBI
CHEBI:8068
EC Number
216-950-6

Properties

Computed structural properties

Topological polar surface area
21.3 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
14
Formal charge
0
Complexity
154

Experimental & physicochemical properties

Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Safety & regulation

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

GHS classification

GHS Classification · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Toxicology

Health Effects · 1 item

Using large amounts of these drugs can result in a condition known as amphetamine psychosis -- which can result in auditory, visual and tactile hallucinations, intense paranoia, irrational thoughts and beliefs, delusions, and mental confusion.

Exposure RoutesReadily absorbed from the gastro-intestinal tract and buccal mucosa.
Toxicity Summary · 1 item

Phenmetrazine is thought to block the reuptake of norepinephrine and dopamine into the presynaptic neuron leading to an increase in the release of these monoamines into the extraneuronal space. Dopamine integrates incoming sensory stimuli, initiates and controls fine movement (nigro-neostriatal pathway), controls emotional behavior (midbrain mesolimbic-forebrain system) and controls hypothalamic-pituitary endocrine system (tubero-infundibular system). It is this latter effect on the tubero-infundibular systm that seems to lead to reduced food intake. Phenmetrazine also acts as a monoamine oxidase inhibitor.

Signs and Symptoms · 1 item

Symptoms of overdose include acute central nervous system stimulation, cardiotoxicity causing tachycardia, arrhythmias, hypertension, and cardiovascular collapse. Whilst some patients show signs of toxicity at blood concentrations of 20 µg/L, chronic abusers of amphetamine have been known to have blood concentration of up to 3000 µg/L.

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Primarily hepatic (via CYP3A and CYP2D6). Resistant to metabolism by monoamine oxidase. Metabolism involves deamination to para-hydroxyamphetamine and phenylacetone; this latter compound is subsequently oxidize to benzoic acid and excreted as glucuronide or glycine (hippuric acid) conjugate. Smaller amounts of amphetamine are converted to norephedrine by oxidation. Half Life: 16 to 31 hours

MeSH Pharmacological Classification · 3 items

A loosely defined group of drugs that tend to increase behavioral alertness, agitation, or excitation. They work by a variety of mechanisms, but usually not by direct excitation of neurons. The many drugs that have such actions as side effects to their main therapeutic use are not included here.

Agents that are used to suppress appetite.

Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.

Uses & manufacturing

UsesUsed as an anorectic in the treatment of obesity.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataAdult monkeys have an LD<sub>50</sub> of 15 to 20 mg/kg, whereas for young monkeys the LD<sub>50</sub> is only 5 mg/kg. (A308)