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Para-Methoxymethamphetamine
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Para-Methoxymethamphetamine
para-Methoxymethamphetamine (PMMA), also known as 4-methoxy-N-methylamphetamine (4-MMA), is a serotonergic drug of the amphetamine family related to para-methoxyamphetamine (PMA). It is the 4-methoxy analogue of methamphetamine. Little is known about the pharmacological properties, metabolism, and toxicity of PMMA; because of its structural similarity to PMA, which has known toxicity in humans, it is thought to have considerable potential to cause harmful side effects or death in overdose. In the early 2010s, a number of deaths in users of the drug MDMA were linked to misrepresented tablets and capsules of PMMA.
PMMA is a serotonin–norepinephrine releasing agent (SNRA) as well as potent monoamine oxidase inhibitor (MAOI). Its effects in humans are reputedly similar to those of PMA, but slightly more empathogenic in nature.[medical citation needed] It has a reduced tendency to produce severe hyperthermia at low dosages, but at higher dosages side effects and risk of death become similar to those of PMA.
The synthesis and effects of PMMA were described by American experimental chemist Alexander Shulgin in his book PiHKAL, where it is referred to by the name "methyl-MA", as the N-methylated form of 4-MA (PMA).
According to Alexander Shulgin in PiHKAL, the effects of PMMA at 110 mg included tachycardia, compulsive yawning, and nystagmus, among others. It was said to have some of the physical side effects of the entactogen MDMA but none of its central effects. No psychedelic-like effects were mentioned. In rodents, PMMA produces hyperlocomotion, no changes in locomotor activity, and/or catatonia, and has effects that are said to differ from those of amphetamine-like stimulants. It has been said not to have amphetamine-like properties in rodents even at high doses. Similarly, PMMA did not substitute for the psychedelic DOM. On the other hand, in contrast to PMA, PMMA fully substituted for MDMA in drug discrimination tests in rodents, despite not having MDMA-like psychoactive effects in humans. In any case, PMMA is said to lack the amphetamine- or stimulant-like properties of MDMA.
PMMA is a monoamine releasing agent (MRA). The drug's EC50 values for induction of monoamine release in rat brain synaptosomes have been reported for the individual enantiomers of PMMA. In the case of (S)-PMMA, they are 41 nM for serotonin, 147 nM for norepinephrine, and 1,000 nM for dopamine, whereas for (R)-PMMA, they are 134 nM for serotonin, >14,000 nM for norepinephrine, and 1,600 nM for dopamine. Hence, PMMA appears to be a serotonin–norepinephrine releasing agent (SNRA) with weak effects on dopamine. The drug has been found to strongly release serotonin and to weakly release dopamine in the brain in rodents in vivo.
In addition to its MRA activity, PMMA is a potent monoamine oxidase A (MAO-A) inhibitor. Its IC50 for MAO-A inhibition has been reported to be 1,700 nM. This is several-fold less potent than the related agents para-methoxyamphetamine (PMA) and 4-methylthioamphetamine (4-MTA).
PMMA is said to lack affinity for the serotonin 5-HT2A receptor. In one study, its affinities were >20,000 nM for the serotonin 5-HT1A receptor, 13,600 nM for the serotonin 5-HT2A receptor, and >13,000 nM for the serotonin 5-HT2C receptor. On the other hand, PMMA shows much higher affinities for the mouse and rat trace amine-associated receptor 1 (TAAR1).
PMMA has been found in tablets and capsules of the MDMA sold as "ecstasy". A number of deaths have been attributed to tablets sold as ecstasy that contained other substances, such as PMMA's structural analog, PMA. Death can occur when an ecstasy user believes they are consuming recreational doses of MDMA, when they are in fact consuming a lethal dose of another substance with similar effects. PMA is of particular concern because it not only causes a release of serotonin but also acts as a monoamine oxidase inhibitor (MAOI); if it is used in combination with MDMA or another MDMA-like substance, serotonin syndrome can result.
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Para-Methoxymethamphetamine
para-Methoxymethamphetamine (PMMA), also known as 4-methoxy-N-methylamphetamine (4-MMA), is a serotonergic drug of the amphetamine family related to para-methoxyamphetamine (PMA). It is the 4-methoxy analogue of methamphetamine. Little is known about the pharmacological properties, metabolism, and toxicity of PMMA; because of its structural similarity to PMA, which has known toxicity in humans, it is thought to have considerable potential to cause harmful side effects or death in overdose. In the early 2010s, a number of deaths in users of the drug MDMA were linked to misrepresented tablets and capsules of PMMA.
PMMA is a serotonin–norepinephrine releasing agent (SNRA) as well as potent monoamine oxidase inhibitor (MAOI). Its effects in humans are reputedly similar to those of PMA, but slightly more empathogenic in nature.[medical citation needed] It has a reduced tendency to produce severe hyperthermia at low dosages, but at higher dosages side effects and risk of death become similar to those of PMA.
The synthesis and effects of PMMA were described by American experimental chemist Alexander Shulgin in his book PiHKAL, where it is referred to by the name "methyl-MA", as the N-methylated form of 4-MA (PMA).
According to Alexander Shulgin in PiHKAL, the effects of PMMA at 110 mg included tachycardia, compulsive yawning, and nystagmus, among others. It was said to have some of the physical side effects of the entactogen MDMA but none of its central effects. No psychedelic-like effects were mentioned. In rodents, PMMA produces hyperlocomotion, no changes in locomotor activity, and/or catatonia, and has effects that are said to differ from those of amphetamine-like stimulants. It has been said not to have amphetamine-like properties in rodents even at high doses. Similarly, PMMA did not substitute for the psychedelic DOM. On the other hand, in contrast to PMA, PMMA fully substituted for MDMA in drug discrimination tests in rodents, despite not having MDMA-like psychoactive effects in humans. In any case, PMMA is said to lack the amphetamine- or stimulant-like properties of MDMA.
PMMA is a monoamine releasing agent (MRA). The drug's EC50 values for induction of monoamine release in rat brain synaptosomes have been reported for the individual enantiomers of PMMA. In the case of (S)-PMMA, they are 41 nM for serotonin, 147 nM for norepinephrine, and 1,000 nM for dopamine, whereas for (R)-PMMA, they are 134 nM for serotonin, >14,000 nM for norepinephrine, and 1,600 nM for dopamine. Hence, PMMA appears to be a serotonin–norepinephrine releasing agent (SNRA) with weak effects on dopamine. The drug has been found to strongly release serotonin and to weakly release dopamine in the brain in rodents in vivo.
In addition to its MRA activity, PMMA is a potent monoamine oxidase A (MAO-A) inhibitor. Its IC50 for MAO-A inhibition has been reported to be 1,700 nM. This is several-fold less potent than the related agents para-methoxyamphetamine (PMA) and 4-methylthioamphetamine (4-MTA).
PMMA is said to lack affinity for the serotonin 5-HT2A receptor. In one study, its affinities were >20,000 nM for the serotonin 5-HT1A receptor, 13,600 nM for the serotonin 5-HT2A receptor, and >13,000 nM for the serotonin 5-HT2C receptor. On the other hand, PMMA shows much higher affinities for the mouse and rat trace amine-associated receptor 1 (TAAR1).
PMMA has been found in tablets and capsules of the MDMA sold as "ecstasy". A number of deaths have been attributed to tablets sold as ecstasy that contained other substances, such as PMMA's structural analog, PMA. Death can occur when an ecstasy user believes they are consuming recreational doses of MDMA, when they are in fact consuming a lethal dose of another substance with similar effects. PMA is of particular concern because it not only causes a release of serotonin but also acts as a monoamine oxidase inhibitor (MAOI); if it is used in combination with MDMA or another MDMA-like substance, serotonin syndrome can result.
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