3-Methylthiofentanyl

Last updated
3-Methylthiofentanyl
3-Methylthiofentanyl.svg
Clinical data
Other namesN-[3-methyl-1-(2-thiophen-2-ylethyl)-4-piperidyl]-N-phenyl-propanamide; 3-methyl-thiofentanyl
Legal status
Legal status
Identifiers
  • (RS)-N-{3-Methyl-1-[2-(2-thienyl)ethyl]piperidin-4-yl}-N-phenylpropanamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
Chemical and physical data
Formula C21H28N2OS
Molar mass 356.53 g·mol−1
3D model (JSmol)
  • O=C(N(c1ccccc1)C2CCN(CC2C)CCc3sccc3)CC
  • InChI=1S/C21H28N2OS/c1-3-21(24)23(18-8-5-4-6-9-18)20-12-14-22(16-17(20)2)13-11-19-10-7-15-25-19/h4-10,15,17,20H,3,11-14,16H2,1-2H3 Yes check.svgY
  • Key:SRARDYUHGVMEQI-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

3-Methylthiofentanyl is an opioid analgesic and analogue of fentanyl.

3-Methylthiofentanyl was sold briefly on the black market in the early 1980s, before the introduction of the Federal Analog Act which for the first time attempted to control entire families of drugs based on their structural similarity rather than scheduling each drug individually as they appeared. [1]

3-Methylthiofentanyl has similar effects to fentanyl. Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear. [2]

See also

Related Research Articles

<span class="mw-page-title-main">Parafluorofentanyl</span> Opioid analgesic

Parafluorofentanyl is an opioid analgesic analogue of fentanyl developed by Janssen Pharmaceuticals in the 1960s.

<span class="mw-page-title-main">Thiofentanyl</span> Opioid

Thiofentanyl is an opioid analgesic that is an analogue of fentanyl.

<span class="mw-page-title-main">Betahydroxythiofentanyl</span> Chemical compound

Betahydroxythiofentanyl (β-hydroxythiofentanyl) is an opioid analgesic that is an analog of fentanyl. Beginning as early as 2008, clandestine labs in China began to manufacture synthetic opioids on an industrial scale. Initially, these opioids were distributed in Eastern European markets such as Ukraine and Estonia. Beginning in 2015, fentanyl had replaced heroin as the opioid of choice due to its cheap cost of production and astronomical potency. Utilizing loosely regulated drug laws in the ports of western Mexico, Mexican and Chinese criminal organizations began to traffic the drug en masse along the U.S.-Mexico border.

α-Methylthiofentanyl Chemical compound

α-Methylthiofentanyl is an opioid analgesic that is an analogue of fentanyl.

<span class="mw-page-title-main">Betahydroxyfentanyl</span> Opioid analgesic

β-Hydroxyfentanyl (Fentanol) is an opioid analgesic that is an analogue of fentanyl.

<span class="mw-page-title-main">Trefentanil</span> Chemical compound

Trefentanil (A-3665) is an opioid analgesic that is an analogue of fentanyl and was developed in 1992.

<span class="mw-page-title-main">Brifentanil</span> Chemical compound

Brifentanil (A-3331) is an opioid analgesic that is an analogue of fentanyl and was developed in the early 1990s.

<span class="mw-page-title-main">Lofentanil</span> Opioid analgesic

Lofentanil or lofentanyl is one of the most potent opioid analgesics known and is an analogue of fentanyl, which was developed in 1960. It is most similar to the highly potent opioid carfentanil (4-carbomethoxyfentanyl), only slightly more potent. Lofentanil can be described as 3-methylcarfentanil, or 3-methyl-4-carbomethoxyfentanyl. While 3-methylfentanyl is considerably more potent than fentanyl itself, lofentanil is only slightly stronger than carfentanil. This suggests that substitution at both the 3 and 4 positions of the piperidine ring introduces steric hindrance which prevents μ-opioid affinity from increasing much further. As with other 3-substituted fentanyl derivatives such as ohmefentanyl, the stereoisomerism of lofentanil is very important, with some stereoisomers being much more potent than others.

<span class="mw-page-title-main">3-Allylfentanyl</span> Opioid analgesic

3-Allylfentanyl is an opioid analgesic that is an analogue of fentanyl.

<span class="mw-page-title-main">Phenaridine</span> Opioid analgesic

Phenaridine (2,5-dimethylfentanyl) is an opioid analgesic that is an analogue of fentanyl. It was developed in 1972, and is used for surgical anasthesia.

<i>beta</i>-Methylfentanyl Opioid analgesic

β-Methylfentanyl is an opioid analgesic that is an analogue of fentanyl.

<span class="mw-page-title-main">R-30490</span> Opioid analgesic

R-30490 is an opioid analgesic related to the highly potent animal tranquilizer carfentanil, and with only slightly lower potency. It was first synthesised by a team of chemists at Janssen Pharmaceutica led by Paul Janssen, who were investigating the structure-activity relationships of the fentanyl family of drugs. R-30490 was found to be the most selective agonist for the μ-opioid receptor out of all the fentanyl analogues tested, but it has never been introduced for medical use in humans, although the closely related drug sufentanil is widely used for analgesia and anesthesia during major surgery.

<span class="mw-page-title-main">Butyrfentanyl</span> Synthetic opioid analgesic

Butyrfentanyl or butyrylfentanyl is a potent short-acting synthetic opioid analgesic drug. It is an analog of fentanyl with around one quarter of its potency. One of the first mentions of this drug can be found in document written by The College on Problem of Drug Dependence, where it is mentioned as N-butyramide fentanyl analog. This document also states that the article describing its clinical effects was published in 1987. It is an agonist for the μ-opioid receptors.

<span class="mw-page-title-main">3-Methylbutyrfentanyl</span> Opioid analgesic

3-Methylbutyrfentanyl (3-MBF) is an opioid analgesic that is an analog of butyrfentanyl.

<span class="mw-page-title-main">Acrylfentanyl</span> Opioid analgesic

Acrylfentanyl (also known as acryloylfentanyl or Egyptenyl) is a highly potent opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug. In animal studies the IC50 or half maximal inhibitory concentration for acrylfentanyl to displace naloxone is 1.4 nM, being slightly more potent than fentanyl itself (1.6 nM) as well as having a longer duration of action.

<span class="mw-page-title-main">Orthofluorofentanyl</span> Opioid analgesic

Orthofluorofentanyl is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug. While the structural isomer p-fluorofentanyl was one of the first illicit fentanyl analogues identified in 1981, Orthofluorofentanyl did not appear on the illicit market until August 2016.

<span class="mw-page-title-main">Isobutyrylfentanyl</span> Opioid analgesic

Isobutyrylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug. It is believed to be around the same potency as butyrfentanyl but has been less widely distributed on illicit markets, though it was one of the earliest of the "new wave" of fentanyl derivatives to appear, and was reported in Europe for the first time in December 2012.

<span class="mw-page-title-main">Benzoylfentanyl</span> Opioid analgesic

Benzoylfentanyl, also known as phenylfentanyl, is an opioid analgesic that is an analog of fentanyl and has been sold as a designer drug. In the United States, benzoylfentanyl was first identified in Drug Enforcement Administration drug seizures in 2018.

<span class="mw-page-title-main">Isofentanyl</span> Chemical compound

Isofentanyl (3-methyl-benzylfentanyl) is an opioid analgesic that is an analog of fentanyl first invented in 1973, and which has been sold as a designer drug.

<span class="mw-page-title-main">2,2'-Difluorofentanyl</span> Chemical compound

2,2'-Difluorofentanyl is an opioid analgesic that is an analog of fentanyl which has been sold as a designer drug.

References

  1. Henderson, GL (1988). "Designer Drugs: Past History and Future Prospects". Journal of Forensic Sciences. 33 (2): 569–575. doi:10.1520/JFS11976J. PMID   3286815.
  2. Mounteney J, Giraudon I, Denissov G, Griffiths P (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal of Drug Policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID   25976511.