Diethylcathinone
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(Redirected from Diethylpropion)
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| Systematic (IUPAC) name | |
|---|---|
| 2-(diethylamino)-1-phenylpropan-1-one | |
| Identifiers | |
| CAS number | 90-84-6 |
| ATC code | A08AA03 |
| PubChem | 7029 |
| Chemical data | |
| Formula | C13H19NO |
| Mol. mass | 205.30 |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
B |
| Legal status | |
| Routes | ? |
Diethylcathinone (also called diethylpropion and amfepramone), is a sympathomimetic stimulant drug marketed as an appetite suppressant. It is sold under the brand name Tenuate or Tenuate Dospan, and may also be known as amfepramone.
The popular antidepressant, bupropion (Wellbutrin) is an analogue of this chemical. Both diethylpropion and bupropion have a stimulant effect on the central nervous system.
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[edit] Pharmacology
Diethylpropion is a prodrug.[1] It does not become bioactive until one of the N-ethyl groups in the chemical structure has become dealkylated in vivo.[1]
(Di)ethylpropion is quite a weak dopaminergic – this is in contrast to other monoaminergic based appetite suppressants such as sibutramine, phentermine and amphetamine.
Apparently, it has been found to be potentially neurotoxic in that it causes long-term depletions of 5-HT similar to MDMA.[2] This is somewhat unexpected since neither diethylpropion nor ethylpropion are serotonin releasers.[1] Additionally, ethylpropion only weakly interacts with the SERT (Ki >2000nM) whereas diethypropion is completely active at this transporter.[1]
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| Test Drug | Release NET EC50 (nM ± SD) |
NE Uptake Ki (nM ± SD) |
Release DAT EC50 (nM ± SD) |
DA Uptake Ki (nM ± SD) |
Release SERT EC50 (nM ± SD) |
5-HT Uptake Ki (nM ± SD) |
| Phentermine | 39.4 ± 6.6 | - | 262 ± 21 | - | 3,511 ± 253 | - |
| (+)-Amphetamine | 7.07 ± 0.95 | - | 24.8 ± 3.5 | - | 1,765 ± 94 | - |
| Diethylpropion | >10,000 | >10,000 | >10,000 | >10,000 | >10,000 | >10,000 |
| N-Ethylpropion | 99.3 ± 6.6 | - | - | 1,014 ± 80 | 2,118 ± 98 | - |
| Phendimetrazine | 8,300 ± 445 | >10,000 | 19,000 ± 537 | >10,000 | >100,000 | >100,000 |
| Phenmetrazine | 50.4 ± 5.4 | - | 131 ± 11 | - | 7,765 ± 610 | - |
Chemically, it is the N,N-diethyl homologue of cathinone and dimethylcathinone.
Diethylpropion is manufactured in 25 mg tablets and 75 mg controlled-release tablets (Tenuate, Tepanil Ten-Tab).
Diethylpropion is classified as a Schedule IV controlled substance in the United States.
It is also used in the treatment of migraine (off-label).
[edit] Contraindications
- Hypersensitivity to sympathomimetic amines
- Advanced arteriosclerosis or symptomatic cardiovascular disease
- Moderate or severe hypertension
- Hyperthyroidism
- History of drug abuse
- MAO inhibitor use (within 14 days)
[edit] Side effects
- Severe
- Tachycardia, hypertension, arrhythmia, chest pain
- Ear, nose, and throat
- Xerostomia, metallic taste
- Changes in libido, gynecomastia, menstrual irregularities
- Eye
- Blurred vision
- Nausea/vomiting, constipation, abdominal cramps
- Bone marrow depression, agranulocytosis, leukopenia
- Tremor
- Euphoria, agitation, nervousness, restlessness, dizziness, anxiety, headache, mental depression, seizures
- Rash, hives, alopecia, ecchymosis
- Changes in libido, impotence
[edit] See also
[edit] References
- ^ a b c d Rothman RB, Baumann MH. Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. PMID 17017961
- ^ Kleven et al., unpublished data Methamphetamine-induced Neurotoxicity: Structure Activity Relationships Annals of the New York Academy of Sciences Volume 654, pg 292–301
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