ContaminantDB: Phentermine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (7)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:15 UTC

Update Date

2026-05-14 16:24:34 UTC

Accession Number

CHEM002141

Identification

Common Name

Phentermine

Class

Small Molecule

Description

Phentermine is only found in individuals that have used or taken this drug. It is a central nervous system stimulant and sympathomimetic with actions and uses similar to those of dextroamphetamine. It has been used most frequently in the treatment of obesity. Phentermine is an amphetamine that stimulates neurons to release or maintain high levels of a particular group of neurotransmitters known as catecholamines; these include dopamine and norepinephrine. High levels of these catecholamines tend to suppress hunger signals and appetite. The drug seems to inhibit reuptake of noradrenaline, dopamine, and seratonin through inhibition or reversal of the reuptake transporters. It may also inhibit MAO enzymes leaving more neurotransmitter available at the synapse.Phentermine (through catecholamine elevation) may also indirectly affect leptin levels in the brain. It is theorized that phentermine can raise levels of leptin which signal satiety. It is also theorized that increased levels of the catecholamines are partially responsible for halting another chemical messenger known as neuropeptide Y. This peptide initiates eating, decreases energy expenditure, and increases fat storage.

Contaminant Sources

Clean Air Act Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Adrenergic Agent
Amine
Anorexigenic Agent
Appetite Depressant
Central Nervous System Agent
Central Nervous System Stimulant
Drug
Human Neurotoxin
Metabolite
Organic Compound
Stimulant
Sympathomimetic
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
alpha,alpha-Dimethylphenethylamine	ChEBI
Fentermina	ChEBI
Phenterminum	ChEBI
a,a-Dimethylphenethylamine	Generator
Α,α-dimethylphenethylamine	Generator
(alpha,alpha)-Dimethylphenethylamine	HMDB
Adipex p	HMDB
Adipex-p	HMDB
Duromine	HMDB
Hydrochloride, phentermine	HMDB
Ionamine	HMDB
Phentermine hydrochloride	HMDB
AdipexP	HMDB

Chemical Formula

C₁₀H₁₅N

Average Molecular Mass

149.233 g/mol

Monoisotopic Mass

149.120 g/mol

CAS Registry Number

122-09-8

IUPAC Name

2-methyl-1-phenylpropan-2-amine

Traditional Name

phentermine

SMILES

CC(C)(N)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C10H15N/c1-10(2,11)8-9-6-4-3-5-7-9/h3-7H,8,11H2,1-2H3

InChI Key

DHHVAGZRUROJKS-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Amphetamines and derivatives

Alternative Parents

Substituents

Amphetamine or derivatives
Phenylpropane
Aralkylamine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Primary aliphatic amine
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

primary amine (CHEBI:8080 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	205°C
Boiling Point	Not Available
Solubility	18.6 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.76 g/L	ALOGPS
logP	2.32	ALOGPS
logP	2.08	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	10.25	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	48.34 m³·mol⁻¹	ChemAxon
Polarizability	17.87 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9000000000-4b4613b0051412392011	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 80V, Positive	splash10-0006-9000000000-1317a1dff976bad4f840	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0006-9100000000-c3cf4661cf2e9753892b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0006-9000000000-798c9f163004230fe723	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00kf-9000000000-356c0f3eb16f8fe213c0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00kf-9000000000-12472f6717ab22723d53	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0006-9000000000-d5cc268e81c53c1db691	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-bfce4f0893d61e18c642	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0006-9000000000-4027bc21c9067b2afaaf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 65V, Positive	splash10-0006-9000000000-78df824f14afb3ef5819	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9000000000-162a1d1b79c4d13aa4d0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-014l-9000000000-9d917981d06565d9120a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-014i-9000000000-2ee6ba63f942e329e01b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-014l-9000000000-87fec87ba12fab4c26b6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 70V, Positive	splash10-0006-9000000000-6482075e713588714fc7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0006-9000000000-a9d629ba954d37de1894	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 25V, Positive	splash10-0006-9000000000-2edf07337f14f6bb795a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 80V, Positive	splash10-0006-9000000000-57fedb34031977b99d69	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-40c3cdc442be6ab34e41	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00dr-9200000000-e6e9a40aadab17c1eb7d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ue9-0900000000-f2eb273dfd0ec45869c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f89-2900000000-f527ee48b9e2784c178c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0159-4900000000-548f73a83354267c9f81	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-c7ab0aa268d14ae3da39	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1900000000-ce1c08c021fbc1cc5c8c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-2900000000-94b2b38953d359938c0a	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9100000000-7037d3f1fad22de72c33	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Phentermine is rapidly absorbed after oral ingestion.

Mechanism of Toxicity

Phentermine is an amphetamine that stimulates neurons to release or maintain high levels of a particular group of neurotransmitters known as catecholamines; these include dopamine and norepinephrine. High levels of these catecholamines tend to suppress hunger signals and appetite. The drug seems to inhibit reuptake of noradrenaline, dopamine, and seratonin through inhibition or reversal of the reuptake transporters. It may also inhibit MAO enzymes leaving more neurotransmitter available at the synapse.Phentermine (through catecholamine elevation) may also indirectly affect leptin levels in the brain. It is theorized that phentermine can raise levels of leptin which signal satiety. It is also theorized that increased levels of the catecholamines are partially responsible for halting another chemical messenger known as neuropeptide Y. This peptide initiates eating, decreases energy expenditure, and increases fat storage.

Metabolism

Hepatic. Half Life: 16 to 31 hours

Toxicity Values

LD50: 15 to 20 mg/kg (monkey).

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment and management of obesity.

Minimum Risk Level

Not Available

Health Effects

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. 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.

Symptoms

Symptoms of overdose include delirium, mania, self-injury, marked hypertension, tachycardia, arrhythmia, hyperpyrexia, convulsion, coma, and circulatory collapse.

Treatment

Management of acute phentermine intoxication is largely symptomatic and includes lavage and sedation with a barbiturate. Acidification of the urine increases phentermine excretion. Intravenous phentolamine (REGITINE) has been suggested for possible acute, severe hypertension, if this complicates phentermine overdosage. (4)

Concentrations

Not Available

External Links

DrugBank ID

DB00191

HMDB ID

HMDB0014337

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID