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| Formula | C14H19NO3 |
| Molar mass | 249.310 g·mol−1 |
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N,N-Dimethylpentylone (also known as Dipentylone or simply Dimethylpentylone) is a substituted cathinone derivative with stimulant effects, [1] which has been sold as a designer drug, [2] [3] first detected in Sweden in 2014. [4]
Pentylone is a known metabolite of dimethylpentylone.[ medical citation needed ]
Dimethylpentylone was first identified in toxicology samples in the US in late 2021 and has been tracked by the Center for Forensic Science Research and Education (CFSRE) through its NPS Discovery program as an increasingly common drug mismarketed as MDMA where Eutylone was previously commonly mismarketed as MDMA. [5]
On June 26, 2023, the United States Customs and Border Protection seized 32.2 kilograms of dimethylpentylone, sent from China labeled as "beauty products" mailed to an address in Washington, D.C. [6] [7]
On July 10, 2023, Jacksonville DEA Assistant Special Agent in Charge Mike Dubet gave an interview to WJXT (news4jax) reporting that dimethylpentylone has been found in possession by people attending nightclubs and bars in the Jacksonville, Florida area. [8]
Dimethylpentylone is not specifically listed in the United States Controlled Substance Act but would be considered Schedule I as a positional isomer of the Schedule I substance N-Ethylpentylone in the United States, defined as "all isomers" within that definition. [9] [10]
A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. Designer drugs include psychoactive substances that have been designated by the European Union as new psychoactive substances (NPS) as well as analogs of performance-enhancing drugs such as designer steroids. Some of these were originally synthesized by academic or industrial researchers in an effort to discover more potent derivatives with fewer side effects and shorter duration and were later co-opted for recreational use. Other designer drugs were prepared for the first time in clandestine laboratories. Because the efficacy and safety of these substances have not been thoroughly evaluated in animal and human trials, the use of some of these drugs may result in unexpected side effects.
Butylone, also known as β-keto-N-methylbenzodioxolylbutanamine (βk-MBDB), is an entactogen, psychedelic, and stimulant psychoactive drug of the phenethylamine chemical class. It is the β-keto analogue of MBDB and the substituted methylenedioxyphenethylamine analogue of buphedrone.
α-Pyrrolidinopentiophenone is a synthetic stimulant of the cathinone class developed in the 1960s that has been sold as a designer drug. Colloquially, it is sometimes called flakka. α-PVP is chemically related to pyrovalerone and is the ketone analog of prolintane.
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).
Substituted cathinones, which include some stimulants and entactogens, are derivatives of cathinone. They feature a phenethylamine core with an alkyl group attached to the alpha carbon, and a ketone group attached to the beta carbon, along with additional substitutions. Cathinone occurs naturally in the plant khat whose leaves are chewed as a recreational drug.
Eutylone is a stimulant and empathogenic compound developed in the 1960s, which is classified as a designer drug. It was first reported to the EMCDDA in 2014 and became widespread internationally in 2019-2020 following bans on the related compound ephylone. It is not a natural, but a synthetic cathinone. In 2021, eutylone was the most common cathinone identified by the Drug Enforcement Administration in the United States.
Benzedrone (4-MBC) is a designer drug which has been found since 2010 as an ingredient in a number of "bath salt" mixes sold as recreational drugs.
4-Ethylmethcathinone (4-EMC) is a recreational designer drug of the stimulant and entactogen class. It is a structural isomer of 4-MEC and 3,4-DMMC. It has been identified in many countries around the world, initially in Europe but was first found in Australia in 2020.
Bath salts are a group of recreational designer drugs. The name derives from instances in which the drugs were disguised as bath salts. The white powder, granules, or crystals often resemble Epsom salts, but differ chemically. The drugs' packaging often states "not for human consumption" in an attempt to circumvent drug prohibition laws. Additionally, they may be mislabeled as plant food, powdered cleaner, and other such products.
N-Ethylbuphedrone is a stimulant of the cathinone class that has been sold as a designer drug. It is the β-ketone analogue of N,alpha-diethylphenylethylamine.
Dibutylone (bk-DMBDB) is a stimulant drug of the amphetamine, phenethylamine, and cathinone drug classes. It is structurally related to butylone, a designer drug that has been detected in products marketed as bath salts or plant food.
3-Methylmethcathinone, also known as 3-MMC and metaphedrone, is a designer drug from the substituted cathinone family. 3-MMC is closely related in structure to the more commonly known illicit drug mephedrone (4-MMC), and is also illegal in most countries that have banned mephedrone due to 3-MMC being a structural isomer of 4-MMC. However, 3-MMC has still appeared on the recreational drug market as an alternative to mephedrone, and was first identified being sold in Sweden in 2012. Unlike some synthetic cathinones, 3-MMC has been evaluated in at least one large mammal study. 3-MMC is a monoamine transporter substrate that potently inhibits norepinephrine uptake and displays more pronounced dopaminergic vs. serotonergic activity.
α-Pyrrolidinohexiophenone is a synthetic stimulant drug of the cathinone class developed in the 1960s which has been reported as a novel designer drug.
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.
N-Ethylpentylone is a substituted cathinone and stimulant drug which was developed in the 1960s.
α-PHiP is a stimulant drug of the cathinone class that has been sold online as a designer drug. It is a positional isomer of pyrovalerone, with the methyl group shifted from the 4-position of the aromatic ring to the 4-position of the acyl chain. In a classic 2006 study of pyrrolidinyl cathinone derivatives by Meltzer et al. at Organix, the alpha-isobutyl derivative of pyrovalerone, O-2494, was found to have the highest potency in vitro as an inhibitor of the dopamine transporter of the alpha substituted derivatives tested; however, it was not until ten years later in July 2016 that α-PHiP was first identified as a designer drug, when it was reported to the EMCDDA by a forensic laboratory in Slovenia.
TH-PVP is a substituted cathinone derivative which has been sold as a designer drug. It was first identified by a forensic laboratory in Hungary in 2015, but has subsequently been found in numerous other countries around the world including Spain, Belgium, Poland, Turkey and Brazil. Pharmacological studies in vitro showed it to inhibit reuptake and promote the release of monoamine neurotransmitters with some selectivity for serotonin, but it failed to produce stimulant effects in animals, and has a pharmacological profile more comparable to that of sedating empathogens such as MDAI and 5-Methyl-MDA.
2-Methylmethcathinone (2-MMC), also known as ortomephedrone is a recreational designer drug with stimulant effects. It is a substituted cathinone derivative, closely related to better known drugs such as 3-methylmethcathinone and 4-methylmethcathinone (mephedrone). It was first identified in Sweden in 2014, and has subsequently been reported in other European countries such as Poland and Spain.
Isohexylone is a recreational designer drug from the substituted cathinone family, with stimulant effects. It was first identified in the United Kingdom in June 2019.
Dimethylone (βk-MDDMA) is a substituted cathinone derivative with stimulant and empathogenic effects. Unlike the corresponding amphetamine derivative MDDM which is thought to be practically inactive, dimethylone substitutes for methamphetamine and MDMA in animal studies and has been sold as a designer drug.
