Dimethocaine

Title: Dimethocaine
CAS Registry Number: 94-15-5
CAS Name: 3-(Diethylamino)-2,2-dimethyl-1-propanol p-aminobenzoate
Additional Names: 3-diethylamino-2,2-dimethylpropyl p-aminobenzoate; 1-aminobenzoyl-2,2-dimethyl-3-diethylaminopropanol; p-aminobenzoate of diethylaminoneopentyl alcohol
Trademarks: Larocaine (Roche)
Molecular Formula: C16H26N2O2
Molecular Weight: 278.39
Percent Composition: C 69.03%, H 9.41%, N 10.06%, O 11.49%
Literature References: Prepn: Mannich, Wilder, Ber. 65, 378 (1932); C. Mannich, US 1889678 (1932). Pharmacology: O. Gebner et al., Arch. Exp. Pathol. Pharmakol. 168, 447 (1932); and toxicology review: A. D. Hirschfelder, R. N. Bieter, Physiol. Rev. 12, 190-282 (1932).
Derivative Type: Hydrochloride
CAS Registry Number: 553-63-9
Molecular Formula: C16H26N2O2.HCl
Molecular Weight: 314.85
Percent Composition: C 61.04%, H 8.64%, N 8.90%, O 10.16%, Cl 11.26%
Properties: Minute crystals or powder, sometimes fine leaflets. Bitter taste. mp 196-197°. One part dissolves in 3 parts water at 20°, more sol in hot water. One part dissolves also in 10 parts of cold alcohol, in 5 parts of boiling alcohol. Practically insol in ether, oils, fats. Aq solns are slightly acid to litmus, and may be sterilized by heating at 105° for 10 minutes. MLD in mice, rabbits (g/kg): 0.30, 0.15 s.c.; 0.04, 0.015 i.v. (Hirschfelder, Bieter).
Melting point: mp 196-197°
Toxicity data: MLD in mice, rabbits (g/kg): 0.30, 0.15 s.c.; 0.04, 0.015 i.v. (Hirschfelder, Bieter)
Therap-Cat: Anesthetic (local).
Keywords: Anesthetic (Local).
Dimethomorph Dimethoxanate Dimethoxane Dimethyl Carbate Dimethyl Carbonate

Dimethocaine
Dimethocaine-structure.svg
Systematic (IUPAC) name
(3-diethylamino-2,2-dimethylpropyl)-4-aminobenzoate
Clinical data
Legal status  ?
Identifiers
CAS number 94-15-5 YesY
553-63-9 (HCl)
ATC code None
PubChem CID 7177
ChemSpider 6909 N
UNII R3L4A6GOWZ YesY
Chemical data
Formula C16H26N2O2 
Mol. mass 278.39
 N (what is this?)  (verify)

Dimethocaine (Larocaine) is a local anesthetic with stimulant properties that some studies have shown to be half the potency of cocaine.[1][2][3] Anecdotal user reports indicate only 2/3 stimulating effects. The drug however also presents strain on the cardiovascular systems, like cocaine (60%), with the potential to induce tachycardia which could be problematic for those who continuously redose. Additional reports of respiratory arrest have been noted.[4]

When a product sold online in the UK in June 2010, advertised as dimethocaine was tested, it was found to in fact be a mixture of caffeine and lidocaine,[5] and the lack of any dopaminergic stimulant ingredient in such mixes may explain the limited recreational effects reported by many users. Other samples tested have however been shown to contain genuine dimethocaine, and one branded "bath salt" product containing primarily dimethocaine as the active ingredient, was noted to have been particularly subject to abuse by intravenous drug users in Ireland.[6]

The p-NH2 pharmacophore in dimethocaine is a relatively uncommon structural feature for a dopamine reuptake inhibitor, although it is also present in other compounds such as GYKI-52895 and RTI-29.