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Routes of administration | Oral, sublingual, insufflated, inhaled (vaporized), intravenous, rectal |
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Pharmacokinetic data | |
Metabolism | Hepatic |
Excretion | Renal |
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CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.230.711 |
Chemical and physical data | |
Formula | C11H17N |
Molar mass | 163.264 g·mol−1 |
3D model (JSmol) | |
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Etilamfetamine (trade names Apetinil and Adiparthrol; also known as N-ethylamphetamine) is a stimulant drug of the phenethylamine and amphetamine chemical classes. It was invented in the early 20th century and was subsequently used as an anorectic or appetite suppressant in the 1950s, [2] but was not as commonly used as other amphetamines such as amphetamine, methamphetamine, and benzphetamine, and was largely discontinued once newer drugs such as phenmetrazine were introduced. It most likely acts primarily as a dopamine releasing agent. [3] Its activity as a norepinephrine or serotonin releasing agent is not known.
The molecular structure of ethylamphetamine is analogous to methamphetamine, with an ethyl group in place of the methyl group. [Note 1] It can also be considered a substituted amphetamine, with an ethyl group on the amphetamine backbone. [Note 2] [Note 3]
Ethylamphetamine can be used as a recreational drug and, while its prevalence is less than amphetamine's, it is still encountered as a substance taken for recreational purposes.
Ethylamphetamine produces effects similar to amphetamine and methamphetamine, though it is of weaker potency.[ citation needed ] At equipotent dosage, ethylamphetamine is subjectively less euphorigenic.[ citation needed ]
Stimulants are a class of drugs that increase the activity of the brain. They are used for various purposes, such as enhancing alertness, attention, motivation, cognition, mood, and physical performance. Some of the most common stimulants are caffeine, nicotine, amphetamines, cocaine, methylphenidate, and modafinil.
Ephedrine is a central nervous system (CNS) stimulant and sympathomimetic agent that is often used to prevent low blood pressure during anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment. It is of unclear benefit in nasal congestion. It can be taken by mouth or by injection into a muscle, vein, or just under the skin. Onset with intravenous use is fast, while injection into a muscle can take 20 minutes, and by mouth can take an hour for effect. When given by injection, it lasts about an hour, and when taken by mouth, it can last up to four hours.
Methcathinone is a monoamine alkaloid and psychoactive stimulant, a substituted cathinone. It is used as a recreational drug due to its potent stimulant and euphoric effects and is considered to be addictive, with both physical and psychological withdrawal occurring if its use is discontinued after prolonged or high-dosage administration. It is usually snorted, but can be smoked, injected, or taken orally.
D-norpseudoephedrine, also known as cathine and (+)-norpseudoephedrine, is a psychoactive drug of the phenethylamine and amphetamine chemical classes which acts as a stimulant. Along with cathinone, it is found naturally in Catha edulis (khat), and contributes to its overall effects. It has approximately 7-10% the potency of amphetamine.
Phenylpropanolamine (PPA), sold under many brand names, is a sympathomimetic agent which is used as a decongestant and appetite suppressant. It was previously commonly used in prescription and over-the-counter cough and cold preparations. The medication is taken by mouth.
3,4-Methylenedioxyamphetamine is an empathogen-entactogen, psychostimulant, 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.
1,3-Benzodioxolyl-N-methylbutanamine (N-methyl-1,3-benzodioxolylbutanamine, MBDB, 3,4-methylenedioxy-N-methyl-α-ethylphenylethylamine) is an entactogen of the phenethylamine chemical class. It is known by the street names Eden and Methyl-J. MBDB is a ring substituted amphetamine and an analogue of MDMA. Like MDMA, it has a methylene dioxy substitution at the 3 and 4 position on the aromatic ring; this is perhaps the most distinctive feature that structurally define analogues of MDMA, in addition to their unique effects, and as a class they are often referred to as "entactogens" to differentiate between typical psychostimulant amphetamines that (as a general rule) are not ring substituted. MBDB differs from MDMA by having an ethyl group instead of a methyl group attached to the alpha carbon; all other parts are identical. Modification at the alpha carbon is uncommon for substituted amphetamines. It has IC50 values of 784 nM against 5-HT, 7825 nM against dopamine, and 1233 nM against norepinephrine. Its metabolism has been described in scientific literature.
Phendimetrazine is a stimulant drug of the morpholine chemical class used as an appetite suppressant.
Phenylacetone, also known as phenyl-2-propanone, is an organic compound with the chemical formula C6H5CH2COCH3. It is a colorless oil that is soluble in organic solvents. It is a mono-substituted benzene derivative, consisting of an acetone attached to a phenyl group. As such, its systematic IUPAC name is 1-phenyl-2-propanone.
2,5-Dimethoxy-4-ethylamphetamine is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin, and was described in his book PiHKAL.
The substituted methylenedioxyphenethylamines represent a diverse chemical class of compounds derived from phenethylamines. This category encompasses numerous psychoactive substances with entactogenic, psychedelic, and/or stimulant properties, in addition to entheogens. These compounds find application as research chemicals, designer drugs, and recreational substances.
Substituted phenethylamines are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine which can be formed by replacing, or substituting, one or more hydrogen atoms in the phenethylamine core structure with substituents.
3,4-Methylenedioxy-N-ethylamphetamine is an empathogenic psychoactive drug. MDEA is a substituted amphetamine and a substituted methylenedioxyphenethylamine. MDEA acts as a serotonin, norepinephrine, and dopamine releasing agent and reuptake inhibitor.
4-Methylamphetamine is a stimulant and anorectic drug of the phenethylamine and amphetamine chemical classes.
3-Fluoroamphetamine is a stimulant drug from the amphetamine family which acts as a monoamine releaser with similar potency to methamphetamine but more selectivity for dopamine and norepinephrine release over serotonin. It is self-administered by mice to a similar extent to related drugs such as 4-fluoroamphetamine and 3-methylamphetamine.
Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents. The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others. Examples of substituted amphetamines are amphetamine (itself), methamphetamine, ephedrine, cathinone, phentermine, mephentermine, tranylcypromine, bupropion, methoxyphenamine, selegiline, amfepramone (diethylpropion), pyrovalerone, MDMA (ecstasy), and DOM (STP).
Phenylisobutylamine, also known as α-ethylphenethylamine, Butanphenamine, B or AEPEA, is a stimulant drug of the phenethylamine class. It is a higher homologue of amphetamine, differing from amphetamine's molecular structure only by the substitution of the methyl group at the alpha position of the side chain with an ethyl group. Compared to amphetamine, phenylisobutylamine has strongly reduced dopaminergic effects, and instead acts as a selective norepinephrine releasing agent. The dextroisomer of phenylisobutylamine partially substitutes for dextroamphetamine in rats.
4-Chlorophenylisobutylamine, also known as 4-chloro-α-ethylphenethylamine, is an entactogen and stimulant drug of the phenethylamine class. It is an analogue of para-chloroamphetamine (PCA) where the alpha position methyl has been replaced with an ethyl group.
N-Ethylhexedrone (also known as α-ethylaminocaprophenone, N-ethylnorhexedrone, hexen, and NEH) is a stimulant of the cathinone class that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI) with IC50 values of 0.0978 and 0.0467 μM, respectively. N-Ethylhexedrone was first mentioned in a series of patents by Boehringer Ingelheim in the 1960s which led to the development of the better-known drug methylenedioxypyrovalerone (MDPV). Since the mid-2010s, N-ethylhexedrone has been sold online as a designer drug. In 2018, N-ethylhexedrone was the second most common drug of the cathinone class to be identified in Drug Enforcement Administration seizures.
Butylamphetamine (code name PAL-90), also known as N-butylamphetamine (NBA), is a psychostimulant of the substituted amphetamine family which was never marketed. It is the N-butyl analogue of amphetamine and is approximately 6-fold less potent than amphetamine in rats. The drug has been found to be inactive as a dopamine reuptake inhibitor or releasing agent (IC50Tooltip half-maximal inhibitory concentration and EC50Tooltip half-maximal effective concentration > 10,000 nM, respectively). With regard to structure–activity relationships, the potency of N-substituted amphetamine derivatives decreases with increasing chain length in terms of both in vitro and in vivo activity. The pharmacokinetics of butylamphetamine have been studied in humans. It can be metabolized by CYP2D6 via ring hydroxylation similarly to amphetamine.