U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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4-Methoxymethamphetamine (PMMA, para-Methoxymethamphetamine) is a stimulant and psychedelic drug closely related to the amphetamine-class serotonergic drug para-methoxyamphetamine (PMA). Little is known about the pharmacological properties, metabolism, and toxicity of 4-Methoxymethamphetamine. Because of its structural similarity to para-methoxyamphetamine, 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 4-Methoxymethamphetamine. In 2010–2013, a cluster of 29 fatal poisonings related to the toxic designer drug 4-Methoxymethamphetamine was revealed in Norway. The toxicity of PMMA is regarded as substantially higher than for amphetamine, methamphetamine, and MDMA, as indicated by 131 fatal and 31 nonfatal poisonings associated with the abuse of 4-Methoxymethamphetamine worldwide. The toxicity of 4-Methoxymethamphetamine is positively correlated with the 4-Methoxymethamphetamine dose and the blood drug level, but the existing literature indicates that certain human subjects may have an increased risk of 4-Methoxymethamphetamine toxicity. 4-Methoxymethamphetamine, like PMA most likely acts as a selective serotonin releasing agent (SSRA) with weak effects on dopamine and norepinephrine transporters. However, relative to MDMA, it is considerably less effective as a serotonin releaser with properties more akin to a reuptake inhibitor in comparison. It evokes robust hyperthermia while producing only modest hyperactivity and serotonergic neurotoxicity, substantially lower than that caused by MDMA.
Status:
US Previously Marketed
Source:
VASOCORT HYDROXYAMPHETAMINE HYDROBROMIDE by SKF
(1961)
Source URL:
First marketed in 1935

Class (Stereo):
CHEMICAL (RACEMIC)


Conditions:

Hydroxyamphetamine is a derivative of amphetamines. Hydroxyamphetamine is intended mainly as local eye drops for diagnostic purposes. It is indirect sympathomimetic agent which cause dilation of the eye pupil before diagnostic test. Among the minor side effects from its use are: change in color vision, difficulty seeing at night, dry mouth, headache, increased sensitivity of eyes to sunlight, muscle stiffness or tightness and temporary stinging in the eyes. The main use of hydroxyamphetamines as eye drops is the diagnosis of Horner's syndrome which is characterized by nerve lesions. Hydroxyamphetamine hydrobromide is a component of FDA approved brand drug - Paremyd sterile ophthalmic solution (Hydroxyamphetamine hydrobromide, USP 1.0%, Tropicamide, USP 0.25%). Hydroxyamphetamine is an indirect-acting sympathomimetic, while tropicamide acts as a parasympatholytic.
Amphetamine is also prescribed in enantiopure and prodrug form as dextroamphetamine and lisdexamfetamine respectively. Lisdexamfetamine is structurally different from amphetamine, and is inactive until it metabolizes into dextroamphetamine. Dextroamphetamine is useful for those with ADHD and Narcolepsy. It improves self-control for people who have a hard time naturally controlling themselves. Dextroamphetamine aids a person learning and memory of words, and perhaps makes the brain stronger. When a person given dextroamphetamine is tested, their brain is extremely active in the brain parts required for the test and radically less active in other parts. Short practice sessions with dextroamphetamine have a greater effect on learning than sessions without dextroamphetamine. Dextroamphetamine raises decision-making scores, improves choices, and changes beliefs about rewards; at the same time, dextroamphetamine barely—if at all—affects guesses of time. Those who feel lower amounts of joy from dextroamphetamine have greater impulsivity improvements compared to those who feel extreme happiness. The drug should be avoided for those who have hypersensitivity to amphetamines, a history of drug abuse, cardiovascular diseases, hypertensive disease, hyperthyroidism, or in those with glaucoma. In 1935, the medical community became aware of the stimulant properties of amphetamine, specifically dextroamphetamine, and in 1937 Smith, Kline, and French introduced Dexedrine tablets, under the tradename Dexedrine. In the United States, Dexedrine tablets were approved to treat narcolepsy, attention disorders, depression, and obesity. Dexedrine, along with other sympathomimetic, was eventually classified as schedule II, the most restrictive category possible for a drug with recognized medical uses. The exact mechanism of action is not known. Dextroamphetamine stimulates the release of norepinephrine from central adrenergic receptors. At higher dosages, it causes release of dopamine from the mesocorticolimbic system and the nigrostriatal dopamine systems by reversal of the monoamine transporters. Dextroamphetamine may also act as a direct agonist on central 5-HT receptors and may inhibit monoamine oxidase (MAO). Modulation of serotonergic pathways may contribute to the calming effect.
Status:
First marketed in 1931
Source:
Benzedrine Inhaler
Source URL:

Class (Stereo):
CHEMICAL (RACEMIC)



Amphetamine is a potent central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. Amphetamine was discovered in 1887 and exists as two enantiomers: levoamphetamine and dextroamphetamine. The mode of therapeutic action in ADHD is not known. Amphetamines are thought to block the reuptake of norepinephrine and dopamine into the presynaptic neuron and increase the release of these monoamines into the extraneuronal space. At higher dosages, they cause release of dopamine from the mesocorticolimbic system and the nigrostriatal dopamine systems. Amphetamine may also act as a direct agonist on central 5-HT receptors and may inhibit monoamine oxidase (MAO). In the periphery, amphetamines are believed to cause the release of noradrenaline by acting on the adrenergic nerve terminals and alpha- and beta-receptors. Modulation of serotonergic pathways may contribute to the calming affect. The drug interacts with VMAT enzymes to enhance release of DA and 5-HT from vesicles. It may also directly cause the reversal of DAT and SERT. Several currently prescribed amphetamine formulations contain both enantiomers, including Adderall, Dyanavel XR, and Evekeo, the last of which is racemic amphetamine sulfate. Amphetamine is also prescribed in enantiopure and prodrug form as dextroamphetamine and lisdexamfetamine respectively. Lisdexamfetamine is structurally different from amphetamine, and is inactive until it metabolizes into dextroamphetamine.
Status:
US Previously Marketed
Source:
VASOCORT HYDROXYAMPHETAMINE HYDROBROMIDE by SKF
(1961)
Source URL:
First marketed in 1935

Class (Stereo):
CHEMICAL (RACEMIC)


Conditions:

Hydroxyamphetamine is a derivative of amphetamines. Hydroxyamphetamine is intended mainly as local eye drops for diagnostic purposes. It is indirect sympathomimetic agent which cause dilation of the eye pupil before diagnostic test. Among the minor side effects from its use are: change in color vision, difficulty seeing at night, dry mouth, headache, increased sensitivity of eyes to sunlight, muscle stiffness or tightness and temporary stinging in the eyes. The main use of hydroxyamphetamines as eye drops is the diagnosis of Horner's syndrome which is characterized by nerve lesions. Hydroxyamphetamine hydrobromide is a component of FDA approved brand drug - Paremyd sterile ophthalmic solution (Hydroxyamphetamine hydrobromide, USP 1.0%, Tropicamide, USP 0.25%). Hydroxyamphetamine is an indirect-acting sympathomimetic, while tropicamide acts as a parasympatholytic.
Status:
US Previously Marketed
Source:
VASOCORT HYDROXYAMPHETAMINE HYDROBROMIDE by SKF
(1961)
Source URL:
First marketed in 1935

Class (Stereo):
CHEMICAL (RACEMIC)


Conditions:

Hydroxyamphetamine is a derivative of amphetamines. Hydroxyamphetamine is intended mainly as local eye drops for diagnostic purposes. It is indirect sympathomimetic agent which cause dilation of the eye pupil before diagnostic test. Among the minor side effects from its use are: change in color vision, difficulty seeing at night, dry mouth, headache, increased sensitivity of eyes to sunlight, muscle stiffness or tightness and temporary stinging in the eyes. The main use of hydroxyamphetamines as eye drops is the diagnosis of Horner's syndrome which is characterized by nerve lesions. Hydroxyamphetamine hydrobromide is a component of FDA approved brand drug - Paremyd sterile ophthalmic solution (Hydroxyamphetamine hydrobromide, USP 1.0%, Tropicamide, USP 0.25%). Hydroxyamphetamine is an indirect-acting sympathomimetic, while tropicamide acts as a parasympatholytic.