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Clortermine

HCID 25223
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Basic information

CAS
10389-72-7
Standard SMILES
CC(C)(N)Cc1ccccc1Cl
InChIKey
HXCXASJHZQXCKK-UHFFFAOYSA-N
Molecular formula
C10H14ClN
Average molar mass
183.68 g/mol
Monoisotopic mass
183.0814771

Overview

Clortermine is a member of amphetamines.

Names & identifiers

Preferred name
Clortermine
IUPAC
1-(2-chlorophenyl)-2-methylpropan-2-amine
English name
Clortermine
Molecular formula
C10H14ClN
Molecular weight
183.68

Names & synonyms

CLORTERMINE10389-73-81-(2-chlorophenyl)-2-methylpropan-2-amineClorterminaClortermine [INN]o-ChlorophentermineClorterminum1-(o-Chlorophenyl)-2-methyl-2-aminopropaneClorterminum [INN-Latin]Clortermina [INN-Spanish]DTXSID0022850HSDB 3306
Show more names
Chlortermine2-Chloro-α,α-dimethylbenzeneethanamineBenzeneethanamine, 2-chloro-α,α-dimethyl-1-(2-Chlorophenyl)-2-methyl-2-propaneamine1-(2-chlorophenyl)-2-methyl-propan-2-amine[2-(2-chlorophenyl)-1,1-dimethyl-ethyl]amine
UNII-4FA88HM3IX4FA88HM3IX2-Chloro-alpha,alpha-dimethylbenzeneethanamineo-Chloro-alpha,alpha-dimethylphenethylamine1-(o-Chlorophenyl)-2-methyl-2-propylamineCLORTERMINE [MI]Phenethylamine, o-chloro-alpha,alpha-dimethyl-CLORTERMINE [HSDB]

Database identifiers

CAS
10389-72-7、10389-73-8
PubChem CID
25223
DTXSID
DTXSID0022850
ChEMBL
CHEMBL1697833
ChEBI
CHEBI:134826
UNII
4FA88HM3IX
Nikkaji
J10.469H

Properties

Computed structural propertiesFilling in

XLogP
2.5
Topological polar surface area
26 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
12
Formal charge
0
Complexity
145

Experimental & physicochemical properties

Drugs · 4 items

DEA NFLIS-Drug Category -> Stimulants

DEA Schedule III Controlled Substance -> Stimulants

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

Boiling Point116-118 °C @ 16 MM HG
Melting Point · 2 items

245-246

CRYSTALS FROM ETHANOL; MP: 245-246 °C /CLORTERMINE HYDROCHLORIDE/

Physicochemical properties

Boiling point
16 · bp16 116-118°
Density
1.074 · 1.074±0.06 g/cm3(Predicted)
pka
9.6 · 9.60±0.25(Predicted)
FDA UNII
4 FA88HM3IX · 4FA88HM3IX
Hazardous Substances Data
10389 · 10389-73-8(Hazardous Substances Data)
DEA Controlled Substances
1647 CSA · CSCN: 1647CSA SCH: Schedule IIINARC: No

Safety & regulation

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

Hazard information

Regulatory InformationDEA schedule III controlled substance
FDA Requirements · 3 items

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Schedules of controlled substances are established by section 202 of the Controlled Substances Act (21 U.S.C. 812). Schedule III includes clortermine, DEA Code #1647; Drug class: Stimulant.

Drugs; statement of required warning. The label of any drug listed as a "controlled substance" in schedule II, III, or IV of the Federal Controlled Substances Act shall, when dispensed to or for a patient, contain the following warning: "Caution: Federal law prohibits the transfer of this drug to any person other than the patient for whom it was prescribed." This statement is not required to appear on the label of a controlled substance for use in clinical investigations which are "blind".

Toxicology

Toxicity Summary · 1 item

IDENTIFICATION: Clortermine hydrochloride is a centrally acting antiobesity drug. It is an amphetamine derivative and misused for performance enhancement and relief of fatigue. Its abuse is either orally or by injection. HUMAN EXPOSURE: Main risks and target organs: Acute central nervous system stimulation, cardiotoxicity causing tachycardia, arrhythmias, hypertension and cardiovascular collapse. High risk of dependency and abuse. Summary of clinical effects: Cardiovascular: Palpitation, chest pain, tachycardia, arrhythmias and hypertension are common; cardiovascular collapse can occur in severe poisoning. Myocardial ischaemia, infarction and ventricular dysfunction are described. Central Nervous System (CNS): Stimulation of CNS, tremor, restlessness, agitation, insomnia, increased motor activity, headache, convulsions, coma and hyperreflexia are described. Stroke and cerebral vasculitis have been observed. Gastrointestinal: Vomiting, diarrhea and cramps may occur. Genitourinary: Increased bladder sphincter tone may cause dysuria, hesitancy and acute urinary retention. Renal failure can occur secondary to dehydration or rhabdomyolysis. Renal ischemia may be noted. Dermatologic: Skin is usually pale and diaphoretic, but mucous membranes appear dry. Endocrine: Transient hyperthyroxinemia may be noted. Metabolism: Increased metabolic and muscular activity may result in hyperventilation and hyperthermia. Weight loss is common with chronic use. Fluid/Electrolyte: Hypo- and hyperkalemia have been reported. Dehydration is common. Musculoskeletal: Fasciculations and rigidity may be noted. Rhabdomyolysis is an important consequence of severe poisoning. Psychiatric: Agitation, confusion, mood elevation, increased wakefulness, talkativeness, irritability and panic attacks are typical. Chronic abuse can cause delusions and paranoia. A withdrawal syndrome occurs after abrupt cessation following chronic use. Contraindications: Anorexia, insomnia, psychopathic personality disorders, suicidal tendencies, Tourette syndrome and other disorders, hyperthyroidism, narrow angle glaucoma, diabetes mellitis and cardiovascular diseases such as angina, hypertension and arrythmias.Interacts with several other CNS stimulant drugs. Routes of exposure: Oral: Readily absorbed from the gastro-intestinal tract and buccal mucosa. It is resistant to metabolism by monoamine oxidase. Inhalation: Rapidly absorbed by inhalation and is abused by this route. Parenteral: Frequent route of entry in abuse situations. Absorption by route of exposure: Rapidly absorbed after oral ingestion. Peak plasma levels occur within 1 to 3 hours, varying with the degree of physical activity and the amount of food in the stomach. Absorption is usually complete by 4 to 6 hours. Sustained release preparations are available as resin bound, rather than soluble, salts. These compounds display reduced peak blood levels compared with standard preparations, but total amount absorbed and time to peak levels remain similar. Distribution by route of exposure: Concentrated in the kidney, lungs, cerebrospinal fluid and brain. Highly lipid soluble and readily cross the blood-brain barrier. Protein binding and volume of distribution varies widely, but the average volume of distribution is 5 L/kg body weight. Biological half-life by route of exposure: Under normal conditions, about 30% is excreted unchanged in the urine but this excretion is highly variable and is dependent on urinary pH. When the urinary pH is acidic (pH 5.5 to 6.0), elimination is predominantly by urinary excretion with approximately 60% of a dose being excreted unchanged by the kidney within 48 hours. When the urinary pH is alkaline (pH 7.5 to 8.0), elimination is predominantly by deamination (less than 7% excreted unchanged in the urine); the half-life ranging from 16 to 31 hours. Metabolism: The major metabolic pathway involves deamination by cytochrome P450 to the para-hydroxy compound and its congener phenylacetone; this latter compound is subsequently oxidized to chloro benzoic acid and excreted as glucuronide or glycine (hippuric acid) conjugate. Smaller amounts are converted to chloronorephedrine by oxidation. Hydroxylation produces an active metabolite, O-hyroxynorephedrine, which acts as a false neurotransmitter and may account for some drug effect, especially in chronic users. Elimination and excretion: Normally 5 to 30% of a therapeutic dose is excreted unchanged in the urine by 24 hours, but the actual amount of urinary excretion and metabolism is highly pH dependent. Mode of action: Toxicodynamics: Appears to exert most or all of its effect in the CNS by causing release of biogenic amines, especialy norepinephrine and dopamine, from storage sites in nerve terminals. It may also slow down catecholamine metabolism by inhibiting monoamine oxidase. Teratogenicity: Use of the compound for medical indications does not pose a significant risk to the fetus for congenital anomalies. Mild withdrawal symptoms may be observed in the newborn, but the few studies of infant follow-up have not shown long-term sequele, although more studies of this nature are needed. Illicit maternal use or abuse presents a significant risk to the fetus and newborn, including intrauterine growth retardation, premature delivery and the potential for increased maternal, fetal and neonatal morbidity. These poor outcomes are probably multifactorial in origin, involving multiple drug use, life-styles and poor maternal health. However, cerebral injuries occurring in newborns exposed in utero appear to be directly related to the vasoconstrictive properties of the compound. Those children exposed throughout pregnancy tended to be more aggressive. Interactions: Acetazolamide: administration may increase serum concentration. Alcohol: may increase serum concentration. Ascorbic acid: lowering urinary pH, may enhance excretion. Furazolidone: May induce a hypertensive response in patients taking furazolidone. Guanethidine: Inhibits the antihypertensive response to guanethidine. Haloperidol: limited evidence indicates that haloperidol may inhibit the effects but the clinical importance of this interaction is not established. Lithium carbonate: isolated case reports indicate that lithium may inhibit the effects. Monoamine oxidase inhibitor: severe hypertensive reactions have followed the administration to patients taking monoamine oxidase inhibitors. Norepinephrine: Abuse may enhance the pressor response to norepinephrine. Phenothiazines: May inhibit the antipsychotic effect of phenothiazines, and phenothiazines may inhibit the anorectic effect. Sodium bicarbonate: large doses of sodium bicarbonate inhibit its elimination, thus increasing the effect. Tricyclic antidepressants: theoretically increases the effect, but clinical evidence is lacking. /Clortermine hydrochloride/

Chemistry & industry

Pharmacology

Mechanism of Action/CLORTERMINE/ ... IS THE ORTHO-CHLORO ISOMER OF CHLORPHENTERMINE HYDROCHLORIDE, TO WHICH IT IS COMPARABLE IN SUPPRESSING APPETITE. /CLORTERMINE HYDROCHLORIDE/
Biological Half-Life9 to 24 hr /Clortermine hydrochloride/

Uses & manufacturing

UsesMEDICATION
Formulations/PreparationsCHLOROPHENETHYLAMINE HYDROCHLORIDE; S 77 /CLORTERMINE HYDROCHLORIDE/

Applications

UsesAnorexic.

Upstream & downstream products

Upstream raw materials

Acetone

Additional notes

DefinitionChEBI: Clortermine is a member of amphetamines.

Related reactions

3 records
New reaction record
HRID 1542655 reaction equation
HRID 1542655As productTraining data from https://doi.org/10.1039/C8SC04228D (1/10)
HRID 1826893 reaction equation
HRID 1826893As productuspto-grants-2006_05
HRID 2302049 reaction equation
HRID 2302049As productuspto-grants-2002_08

Compound notes

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Human Toxicity Excerpts · 4 items

CARDIOVASCULAR SIDE EFFECTS INCL TACHYCARDIA, PALPITATION, & HYPERTENSION. UNTOWARD EFFECTS ON NERVOUS SYSTEM INCL RESTLESSNESS, EXCITEMENT, INSOMNIA, EUPHORIA, DYSPHORIA, DIZZINESS, TREMOR, HEADACHE, & RARE PSYCHOTIC EPISODES. /CLORTERMINE HYDROCHLORIDE/

OTHER SIDE EFFECTS INCL XEROSTOMIA, UNPLEASANT TASTE, CONSTIPATION, DIARRHEA, GI UPSETS, URTICARIA, IMPOTENCE, & DIMINISHED LIBIDO. /CLORTERMINE HYDROCHLORIDE/

WHEN AMT SUBSTANTIALLY LARGER THAN CLINICAL DOSAGE WERE ADMIN TO VOLUNTEERS, CHILLS, DIZZINESS, NAUSEA, & TREMORS (BUT NO CARDIOVASCULAR EFFECTS) OBSERVED. /CHLORTERMINE HYDROCHLORIDE/

Excessive use may lead to tolerance and physical dependence.

Antidote and Emergency Treatment · 1 item

Diazepam may be given to control central nervous system stimulation and convulsions. For marked excitement or hallucinations chlorpromazine may be necessary and, in addition, its alpha-adrenoceptor blocking properties may be useful for the management of hypertension. Severe hypertension may call for the administration of an alpha-adrenoceptor blocking agent, such as phentolamine. Measures should be taken to control increased body temperature.

Regulatory information

FDA Requirements · 3 items

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Schedules of controlled substances are established by section 202 of the Controlled Substances Act (21 U.S.C. 812). Schedule III includes clortermine, DEA Code #1647; Drug class: Stimulant.

Drugs; statement of required warning. The label of any drug listed as a "controlled substance" in schedule II, III, or IV of the Federal Controlled Substances Act shall, when dispensed to or for a patient, contain the following warning: "Caution: Federal law prohibits the transfer of this drug to any person other than the patient for whom it was prescribed." This statement is not required to appear on the label of a controlled substance for use in clinical investigations which are "blind".

Safety data

DEA Controlled Substances
CSCN: 1647CSA SCH: Schedule IIINARC: No
Hazardous Substances Data
10389-73-8(Hazardous Substances Data)