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Names | |||
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Preferred IUPAC name 4-Methylpentan-2-amine | |||
Other names (4-Methylpentan-2-yl)amine | |||
Identifiers | |||
3D model (JSmol) | |||
ChemSpider | |||
ECHA InfoCard | 100.003.227 | ||
PubChem CID | |||
UNII | |||
CompTox Dashboard (EPA) | |||
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Properties | |||
C6H15N | |||
Molar mass | 101.193 g·mol−1 | ||
Density | 0.717 g/mL [1] | ||
Boiling point | 108–110 °C (226–230 °F; 381–383 K) [1] | ||
Pharmacology | |||
Legal status | |||
Hazards | |||
NFPA 704 (fire diamond) | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
1,3-Dimethylbutylamine (1,3-DMBA, dimethylbutylamine, DMBA, 4-amino-2-methylpentane, or AMP), is a stimulant drug structurally related to methylhexanamine where a butyl group replaces the pentyl group. The compound is an aliphatic amine.
The hydrochloride and citrate salts of DMBA has been identified as unapproved ingredients in some over-the-counter dietary supplements, [3] [4] [5] in which it is used in an apparent attempt to circumvent bans on methylhexanamine. [6] The U.S. Food and Drug Administration (FDA) considers any dietary supplement containing DMBA to be "adulterated". [7] Despite the FDA's opposition, DMBA continues to be sold in the US. [8]
There are no known human safety studies on DMBA and its health effects are entirely unknown. [3] [4] [9]
DMBA is not an agonist of the rodent or human trace amine-associated receptor 1 (TAAR1). [10]
Cathinone is a monoamine alkaloid found in the shrub Catha edulis (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines. It is probably the main contributor to the stimulant effect of Catha edulis, also known as khat. Cathinone differs from many other amphetamines in that it has a ketone functional group. Other phenethylamines that share this structure include the stimulants methcathinone, MDPV, mephedrone and the antidepressant bupropion.
Vardenafil, sold under the brand name Levitra among others, is a medication that is used for treating erectile dysfunction. It is a PDE5 inhibitor. It is taken by mouth.
Nootropics, colloquially brain supplements, smart drugs and cognitive enhancers, are natural, semisynthetic or synthetic compounds which purportedly improve cognitive functions, such as executive functions, attention or memory.
3,4-Methylenedioxyamphetamine (MDA), sometimes referred to as sass, is an empathogen-entactogen, stimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In its pharmacology, MDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal.
Adrafinil, sold under the brand name Olmifon, is a wakefulness-promoting medication that was formerly used in France to improve alertness, attention, wakefulness, and mood, particularly in the elderly. It was also used off-label by individuals who wished to avoid fatigue, such as night workers or others who needed to stay awake and alert for long periods of time. Additionally, the medication has been used non-medically as a novel vigilance-promoting agent.
Phentermine, sold under the brand name Adipex-P among others, is a medication used together with diet and exercise to treat obesity. It is available by itself or as the combination phentermine/topiramate. Phentermine is taken by mouth.
4-Methylaminorex is a stimulant drug of the 2-amino-5-aryloxazoline group that was first synthesized in 1960 by McNeil Laboratories. It is also known by its street name "U4Euh" ("Euphoria"). It is banned in many countries as a stimulant. 4-Methylaminorex has effects comparable to methamphetamine but with a longer duration.
Isometheptene is a sympathomimetic amine sometimes used in the treatment of migraines and tension headaches due to its vasoconstricting properties; that is, it causes constriction (narrowing) of blood vessels. Along with paracetamol and dichloralphenazone, it is one of the constituents of Amidrine.
Aminorex, sold under the brand names Menocil and Apiquel among others, is a weight loss (anorectic) stimulant drug. It was withdrawn from the market after it was found to cause pulmonary hypertension (PPH). In the United States, aminorex is a Schedule I controlled substance.
Picamilon is a drug formed by a synthetic combination of niacin and γ-aminobutyric acid (GABA). It was developed in the Soviet Union in 1969 and further studied in both Russia and Japan as a prodrug of GABA.
β-Methylphenethylamine is an organic compound of the phenethylamine class, and a positional isomer of the drug amphetamine, with which it shares some properties. In particular, both amphetamine and β-methylphenethylamine are human TAAR1 agonists. In appearance, it is a colorless or yellowish liquid.
Trace amine-associated receptor 1 (TAAR1) is a trace amine-associated receptor (TAAR) protein that in humans is encoded by the TAAR1 gene.
Methylhexanamine is an indirect sympathomimetic drug invented and developed by Eli Lilly and Company and marketed as an inhaled nasal decongestant from 1948 until it was voluntarily withdrawn from the market in the 1980s.
Phenpromethamine, also known as N,β-dimethylphenethylamine, is a sympathomimetic nasal decongestant of the phenethylamine group. It was previously marketed as a nasal inhaler from 1943 through 1960 but is no longer available. The medication is a stimulant and is banned by the World Anti-Doping Agency. It has been detected in dietary supplements starting in the 2010s.
Octodrine, also known as dimethylhexylamine (DMHA) and sold under the brand name Vaporpac among others, is a sympathomimetic and stimulant medication that was formerly used in the treatment of hypotension.
Iproheptine, also known as N-isopropyl-1,5-dimethylhexylamine or N-isopropyloctodrine and sold under the brand names Metron and Susat, is a nasal decongestant which has been marketed in Japan. It is described as a vasoconstrictor and antihistamine. The drug is available over-the-counter in Japan.
A monoamine releasing agent (MRA), or simply monoamine releaser, is a drug that induces the release of one or more monoamine neurotransmitters from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrations of the neurotransmitters and hence enhanced signaling by those neurotransmitters. The monoamine neurotransmitters include serotonin, norepinephrine, and dopamine; MRAs can induce the release of one or more of these neurotransmitters.
Pre-workout is a generic term for a range of bodybuilding supplement products used by athletes and weightlifters to enhance athletic performance. Supplements are taken to increase endurance, energy, and focus during a workout. Pre-workout supplements contain a variety of ingredients such as caffeine and creatine, differing by capsule or powder products. The first pre-workout product entered the market in 1982, and since then the category has grown in use. Some pre-workout products contain ingredients linked to adverse effects. Although these products are not regulated, the Food and Drug Administration (FDA) warns consumers to be cautious when consuming them.
Deterenol is a stimulant drug which acts as a beta agonist. It has been found as an ingredient of dietary supplement products, but is banned in most countries due to risk of cardiac arrest.
Oenethyl, also known as 2-methylaminoheptane and sold under the brand names Pacamine and Neosupranol, is a sympathomimetic and vasopressor medication of the alkylamine which is no longer marketed. It was used as a nasal decongestant and to control blood pressure during anesthesia. It is closely structurally related to other alkylamines, for instance methylhexanamine and tuaminoheptane, among others. These compounds are known to act as structurally simple monoamine releasing agents and to produce psychostimulant-like effects.
TAAR1 activation may reduce the rewarding properties of stimulant-type drugs of abuse (AsifMalik et al., 2017; Cotter et al., 2015; Di Cara et al., 2011; Pei et al., 2015; Simmler et al., 2016) and may theoretically counteract addictive properties of other stimulants that are contained in preworkout boosters or used concomitantly. In contrast to phenethylamines, TAAR1 was not activated by the alkylamines 1,3-dimethylamylamine and 1,3-dimethylbutylamine.