2,4-Dichloroamphetamine
(Redirected from Draft:2,4-Dichloroamphetamine)
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| Other names | 2,4-DCA |
| Drug class | Psychostimulant; Serotonergic neurotoxin; Monoamine oxidase inhibitor |
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| Formula | C9H11Cl2N |
| Molar mass | 204.09 g·mol−1 |
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2,4-Dichloroamphetamine (2,4-DCA) is a psychostimulant of the amphetamine family and a potent serotonergic neurotoxin related to para-chloroamphetamine (PCA; 4-chloroamphetamine).[1][2] It is also a potent monoamine oxidase inhibitor in addition to the aforementioned activities.[1][3][2]
See also
[edit]- 3-Chloroamphetamine (3-CA)
- 3,4-Dichloroamphetamine (3,4-DCA)
References
[edit]- ^ a b Biel, J. H.; Bopp, B. A. (1978). "Amphetamines: Structure-Activity Relationships". Stimulants. Boston, MA: Springer US. p. 1–39. doi:10.1007/978-1-4757-0510-2_1. ISBN 978-1-4757-0512-6.
The position of the chloro substituent also markedly affects the activity of the compounps (Table 6). The effect of the meta derivative was approximately equivalent to that of the para derivative but only after inhibition of para-hydroxylation, while the ortho-substituted compound actually slightly raised rather than lowered the serotonin levels (Fuller and Molloy, 1974). The effects of dichloro substitution also varied with the position. 2,4-Dichloroamphetamine was considerably less active as a serotonin depletor than the 4-chloro derivative, but their effects on 5-hydroxyindoleacetic acid were similar due to the potent MAO inhibitor activity of the dichlorinated compound (Fuller and Molloy, 1974). However, the activity of 3,4-dichloroamphetamine was generally comparable to that of p-chloroamphetamine (Pletscher et al., 1964). These observations are consistent with the finding that ortho substitution is detrimental to the serotonin-depleting activity of chlorinated amphetamines.
- ^ a b Fuller, R.W.; Snoddy, H.D.; Roush, Betty W.; Molloy, B.B. (January 1973). "Further structure-activity studies on the lowering of brain 5-hydroxyindoles by 4-chloroamphetamine". Neuropharmacology. 12 (1). Elsevier BV: 33–42. doi:10.1016/0028-3908(73)90129-9. ISSN 0028-3908. PMID 4687274.
- ^ Conde, S.; Madronero, R.; Fernandez-Tome, M. P.; Del Rio, J. (September 1978). "Effects of thiophene analogs of chloroamphetamines on central serotonergic mechanisms". Journal of Medicinal Chemistry. 21 (9). American Chemical Society (ACS): 978–981. doi:10.1021/jm00207a024. ISSN 0022-2623. PMID 722762.
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