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3,4-Dimethoxyphenethylamine
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3,4-Dimethoxyphenethylamine
3,4-Dimethoxyphenethylamine (DMPEA), also known as O,O-dimethyldopamine, is a chemical compound of the phenethylamine class. It is an analogue of the major human neurotransmitter dopamine where the 3- and 4-position hydroxy groups have been replaced with methoxy groups. It is also closely related to mescaline which is 3,4,5-trimethoxyphenethylamine and to 3,4-dimethoxyamphetamine (3,4-DMA).
DMPEA shows weak affinity for serotonin receptors. It induces the head-twitch response, a behavioral proxy of serotonergic psychedelic effects, in rodents. However, according to Alexander Shulgin, it was inactive in humans at doses of 1,000 mg orally and 10 mg intravenously.
DMPEA has some activity as a monoamine oxidase inhibitor.
The elimination half-life of DMPEA is said to be less than 1 hour, indicating rapid and extensive metabolism and inactivation.
One of the earliest syntheses of DMPEA (then referred to as "homoveratrylamine") was that of Pictet and Finkelstein, who made it in a multi-step sequence starting from vanillin. A similar sequence was subsequently reported by Buck and Perkin, as follows:
A much shorter synthesis is given by Shulgin and Shulgin:
DMPEA occurs naturally along with mescaline in various species of cacti such as San Pedro and Peruvian Torch.
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3,4-Dimethoxyphenethylamine
3,4-Dimethoxyphenethylamine (DMPEA), also known as O,O-dimethyldopamine, is a chemical compound of the phenethylamine class. It is an analogue of the major human neurotransmitter dopamine where the 3- and 4-position hydroxy groups have been replaced with methoxy groups. It is also closely related to mescaline which is 3,4,5-trimethoxyphenethylamine and to 3,4-dimethoxyamphetamine (3,4-DMA).
DMPEA shows weak affinity for serotonin receptors. It induces the head-twitch response, a behavioral proxy of serotonergic psychedelic effects, in rodents. However, according to Alexander Shulgin, it was inactive in humans at doses of 1,000 mg orally and 10 mg intravenously.
DMPEA has some activity as a monoamine oxidase inhibitor.
The elimination half-life of DMPEA is said to be less than 1 hour, indicating rapid and extensive metabolism and inactivation.
One of the earliest syntheses of DMPEA (then referred to as "homoveratrylamine") was that of Pictet and Finkelstein, who made it in a multi-step sequence starting from vanillin. A similar sequence was subsequently reported by Buck and Perkin, as follows:
A much shorter synthesis is given by Shulgin and Shulgin:
DMPEA occurs naturally along with mescaline in various species of cacti such as San Pedro and Peruvian Torch.
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