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39-508: (Redirected from China White ) China white , China White or Chinawhite may refer to: China white (drug) , an analog of fentanyl that resembles heroin Arts and entertainment [ edit ] Music [ edit ] China White (band) , a Huntington Beach, California punk rock band "China White", a song by Scorpions on the album Blackout Songs by He Is Legend: "China White" on

78-490: A 1989 Chinese film Chinawhite (nightclub) , London China White (comics) , a villain in the Green Arrow: Year One miniseries See also [ edit ] Chinese white , zinc oxide used as a pigment Topics referred to by the same term [REDACTED] This disambiguation page lists articles associated with the title China white . If an internal link led you here, you may wish to change

117-420: A [1.], [2.], [3.], and [4.] respectively. To further aid in the chemical pedagogy we have aligned each number with a reaction number -> precursor -> product system that follows the following scheme: EXAMPLE: reaction number -> precursor -> product [compound name] 1 -> α -> a [fentanyl] 2 -> β -> b [acetylfentanyl] 3 -> γ -> c [butyrylfentanyl] 4 -> δ -> d [benzoylfentanyl] Using

156-461: A base because of its two amine nitrogens, the secondary amine acts as a base to react with an organic acid which condenses into an amide. Depending on the organic acid used in the amide condensation, different analogues of fentanyl will be produced. To help align this phenomenon in the eyes of chemists, we have numerated the precursor 4-ANPP with a [0.], and then the reactions synthesizing fentanyl, acetylfentanyl, butyrylfentanyl, and benzoylfentanyl with

195-532: A group of Russian chemistry students discovered a simplified synthesis route which used phosgene instead of phenethylamine . Soon, abuse of the drug became widespread, causing a tenth of overdoses in the Moscow region. α-Methylfentanyl became notorious for low safety, and production declined. α-Methylfentanyl has similar effects to fentanyl . It is less potent by weight due to reduced binding affinity to its target site, but has an increased duration of action, as

234-635: A lack of piperidinyl substituents, but this same carbon is a chiral center in both ohm- and lofentanyl because both of those analogues have piperidinyl substituents. The second group are organized into methyl additions, which are known for the fentanyl analogues such as α-methylfentanyl and cis-3-methylfentanyl. These analogues can possess a wide variety of modified pharmacological properties, including increased and decreased potency (receptor binding efficiency), increased or decreased half-life (metabolic binding efficiency) or other side effects on human physiology. Other substituents such as hydroxy, chloro, fluoro, and

273-554: A methylene moiety internally in the ethyl chain within the greater phenethyl moiety. The removal of a methylene, which shortens the chain by one carbon length, creates the benzylfentanyl structure. The addition of a methylene, which lengthens the chain by one length, creates homofentanyl. The modifications covered in this diagram have to do with stereochemistry and the assignment of unique Cahn-Ingold-Prelog R/S assignments to complex analogues of fentanyl. The stereochemistry of fentanyl analgoues can seem at first counter-intuitive, because of

312-585: A reflection of the stereocenter in the piperidine derivative we used being at C-7 position. It is interesting that the C-4 stereocenter, which has no chiral activity in fentanyl (1st example), activiates it in 3-methylfentanyl with an on-the-ring addition, and loses it again in α-methylfentanyl with an off-the-ring addition. The fourth case studied here is ohmfentanyl. Ohmfentanyl has 3 potential stereocenters, which are best analogized by another piperidine derivative: N-(1-hydroxyethyl)-3-methyl-4-hydroxypiperidine. This uses

351-488: A similar structure to analogize the three potential stereocenters in ohmfentanyl, namely the 4-C, the 3-C, and the β-C (beta carbon). These three stereocenters are analogized in the C-4, C-3, and C-7 respectively. When we draw all potential stereoisomers out we see that they are not super-imposable in any combination of pairing, and therefore we have 8 unique stereoisomers and 3 true stereocenters. This yields 8 unique R/S assignment combinations which are outlined as captions under

390-460: A smaller, simpler molecule with the same number of, and dynamics between its, stereocenters. This saves significant space allowing us not to reproduce redundant material that consumes a lot of space on the image. The first case studied here is fentanyl itself, or propionyl-4-anilino-N-phenethylpiperidine, the most well known of the fentanyl analogues and the eponymous molecule (namesake) for the whole chemical categorey. The only identified stereocenter

429-567: A team at Janssen Pharmaceutica in the 1960s. In 1976, it began to appear mixed with heroin, as an additive, and the mixture was sometimes also called "China White". It was first identified in the bodies of two drug overdose victims in Orange County, California , in December 1979, who appeared to have died from opiate overdose but tested negative for any known drugs of this type. Over the next year, there were 13 more deaths, and eventually

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468-459: A wide variety of alkyl groups, are also substituted in place of these methylations to produce psychoactive analogues of fentanyl, but because they often use the same skeletal naming conventions as the simple methyl analogues, we did not reproduce them all in the image here. The modifications described here cover alterations to the ring structure donated by the fentanyl precursor 4-ANPP. Although another series covered substitutions of hydrogen atoms on

507-423: Is found at the 4-carbon, opposite the piperidine nitrogen but adjacent to the aniline nitrogen. This seems to be a stereocenter because of the apparent 4 unique substituents. We transfer this stereocenter to the equivalent molecule cyclohexanol, with an analogous apparent stereocenter. Once we draw out the potential stereoisomers, we see that the two structures are super-imposable in three dimensions, and therefore are

546-495: Is written to help illustrate the basic ring structure of fentanyl and what popular analogues reference on the carbon skeleton, helping a chemist working with fentanyl analogues quickly and consistently navigate the nomenclature system. The synthesis of fentanyl and its analogues are illustrated in these skeletal diagrams. The synthesis of fentalogs is done by reacting the ring structure as a base, 4-ANPP also called 4-anilino-N-phenethylpiperidine and despropionylfentanyl. 4-ANPP acts as

585-591: The DEA , or transnational agencies such as the EMCDDA and UNODC . This is not a comprehensive listing of fentanyl analogues, as more than 1400 compounds from this family have been described in the scientific and patent literature, but it includes many notable compounds that have reached late-stage human clinical trials, or which have been identified as having been sold as designer drugs, as well as representative examples of significant structural variations reported in

624-526: The "cut" in small amounts in normal heroin stamps and bags, making them more potent and profitable than when sold as heroin alone due to the advantage of raising the retail price and potency per unit sold. List of fentanyl analogues This is a list of fentanyl analogues (sometimes referred to as Fentalogs ), including both compounds developed by pharmaceutical companies for legitimate medical use, and those which have been sold as designer drugs and reported to national drug control agencies such as

663-596: The N-[1-(2-phenethyl)-4-piperidyl]aniline nucleus has additional radicals, either alone or in combination, attached as follows: (a) an acetyl, propionyl, butenoyl or butanoyl radical, attached to the aniline nitrogen atom: (b) 1 or more alkyl radicals, with up to 10 carbon atoms in total, attached to the ethyl moiety: (c) any combination of up to 5 alkyl radicals and/or alkoxy radicals (each with up to 6 carbon atoms, including cyclic radicals) and/or halogen radicals, attached to each of

702-496: The above scheme, a chemist can quickly extrapolate the reactions necessary for other fentanyl analogues with more complex organic acids, such as cyclopropryl fentanyl or cyclopentyl fentanyl, or any other fentanyl analogue derived from a reaction of 4-ANPP with a novel organic acid. The modifications covered in this diagram have to do with carbon skeleton modifications of the original fentanyl molecular structure. These are organized into methyl acetate additions, which are most known for

741-752: The album I Am Hollywood "China White II" on the album Suck Out the Poison "China White III" on the album It Hates You "China White (Ten Buck Fuck)" on the Hard Core Logo soundtrack Songs by Dog Fashion Disco: "China White" on the album Erotic Massage "China White" on the European release of the album Committed to a Bright Future "China White" on the album Hoy-Hoy! by Little Feat Chyna Whyte , American rapper, songwriter and author Other uses in arts and entertainment [ edit ] China White (film) ,

780-418: The analysis of stereochemistry in these series of images is the following: This procedure will be used when making an assessment of the number of valid stereoisomers that an analogue of fentanyl will be predicted to have. Because the analogues of fentanyl are so large, and the moieities (sub-regions) of the molecule that are relevant to its chirality are so small, that we often reproduce the fentanyl analogue as

819-486: The benzene rings." A more recent and somewhat broader example was introduced into US Federal legislation in 2018, covering the following structures; "...fentanyl-related substances includes any substance not otherwise controlled in any schedule...that is structurally related to fentanyl by one or more of the following modifications: Because there are so many analogues of fentanyl, the naming for them tends to follow classical or IUPAC nomenclature conventions. This section

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858-419: The class. The weakest compounds such as benzylfentanyl are around the same potency as codeine (i.e. approximately 1/10th the potency of morphine ), while the strongest compounds such as carfentanil and ohmefentanil can be over 10,000x more potent than morphine, meaning there is a 100,000-fold variation in potency between the strongest and weakest fentanyl derivatives. This means that two positional isomers with

897-492: The complex and unique nature of the reasoning organic chemists must develop to internalize complex three dimensional geometries such as those needed to comprehend stereochemistry. Thankfully these images follow a simple procedure for organizing a potential analogue of fentanyl into the total number of unique stereoisomers, the number of true stereocenters on the molecule, and the number of Cahn-Ingold-Prelog R/S assignments that are appropriate for that analogue. The procedure used in

936-414: The fentanyl -> carfentanil conversion. Many analogues of great potency, such as ohmfentanyl and lofentanyl possess methyl acetate groups added to the 4-carbon (of the piperidine ring, in the para- position relative to the annular nitrogen). The methyl acetate is added here from the α-carbon of the acetate moiety as it is with ohm- and lofentanyl. The 4-carbon is not a chiral center in carfetnanil because of

975-407: The four permutations of stereoisomers, none are super-imposable in three dimensions, meaning each is a unique stereoisomer and that both potential stereocenters were true. This gives 4 potential R/S assignments, 1R3S, 1R3R, 1S3S, 1S3R. What is particularly interesting and quite a contrast from the previous example of cyclohexanol, is the stereocenter at C-4 is indeed a true stereocenter here, whereas in

1014-584: The highly potent 3-methylfentanyl , and subsequently by many others such as β-hydroxyfentanyl , ohmefentanyl , β-hydroxythiofentanyl and β-hydroxy-4-methylfentanyl. The development of such a wide structural family of novel narcotic drugs was a major factor responsible for the implementation 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 new drug analogs individually as each appeared. In 1991,

1053-424: The inconsistent use of prime notation . For instance, 4-methylfentanyl, 4'-methylfentanyl and 4"-methylfentanyl are all known compounds, as are 3-methylthio-fentanyl and 3-methyl-thiofentanyl, all of which have varying potencies and pharmacokinetics. Confusion between different positional isomers is especially significant in the case of fentanyls because of the huge variation in potency between different members of

1092-406: The link to point directly to the intended article. Retrieved from " https://en.wikipedia.org/w/index.php?title=China_white&oldid=1186721203 " Category : Disambiguation pages Hidden categories: Short description is different from Wikidata All article disambiguation pages All disambiguation pages China white (drug) α-Methylfentanyl was discovered by

1131-423: The original carbon ring structure, sometimes called functional group additions, this series focuses on the three main modifications to the phenethyl moiety. The first modifications is the removal of the phenthyl moeity from the piperidinyl nitrogen, depicted here as hydrolysis yielding phenethanol. This changes the parent skeletal name to norfentanyl. The second and third modifications are the removal and addition of

1170-481: The other on the C-α (alpha carbon). To analogize these stereocenters we chose N-(1-hydroxyethyl)-4-hydroxypiperidine. When we draw out all potential stereoisomers, we see that the C-4 stereocenter is super-imposable, eliminating it as a true stereocenter. This leaves only 2 R/S assignments that follow the orientation of the stereocenter at the C-α (alpha carbon) position for the real α-methylfentanyl. These are labeled 7S and 7R,

1209-598: The previous example of cyclohexanol as an analogy to fentanyl, the C-4 was not a true stereocenter. This changed because the modification of the C-3 carbon without an equivalent change on the C-2 carbon created an imbalance between two formerly identical substituents, creating a novel stereocenter where there was not one previously. This is why it is so important to follow the 4 steps in the above procedure every time, as "inherited procedural wisdom" may hold an organic chemist back in finding

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1248-498: The responsible agent was identified as α-methylfentanyl. α-Methylfentanyl was placed on the U.S. Schedule I list in September 1981, only two years after its appearance on the street, but already other fentanyl analogs were being developed. Following the appearance of α-methylfentanyl on the market, dozens of new fentanyl analogs have been reported, starting with para-fluorofentanyl , followed by α-methylacetylfentanyl , then by

1287-412: The same molecular weight, which may be difficult to tell apart without detailed chemical analysis, may be hundreds or even thousands of times different in pharmacological potency. Also the wide variety of substitutions that have been used on the basic fentanyl structure, each of which can either reduce or increase the potency, can be unpredictable when used in combination, so it may be impossible to estimate

1326-735: The scientific and patent literature. The structural variations among fentanyl-related substances can impart profound pharmacological differences between these drugs, especially with respect to potency and efficacy. In the United States, the Drug Enforcement Administration placed the broadly defined class of "Fentanyl-Related Substances" on the list of Schedule I drugs in 2018, making it illegal to manufacture, distribute, or possess fentanyl analogs. Temporary control of fentanyl-related substances in Schedule I

1365-415: The self-same molecule. For this reason fentanyl does not have R/S assignments. The second case studied here is of 3-methylfentanyl. There are two potential stereocenters, at the 4-carbon and also at the 3-carbon, where there is additionally a methyl group. Now, we mark both 3 and 4 carbon as potential stereocenters with an asterisk (*), and see how many potential stereoisomers we can eliminate. We see that of

1404-403: The stereoisomers of the analogous molecule. These fundamentals are typically enough to help a chemists navigate the world of fentanyl analogues proficiently. Other substituents and substitutions generally follow the naming conventions outlined in this section. However, the presence of three six-membered rings which can each be independently substituted can easily lead to confusion, especially with

1443-434: The true or correct answer. The third case studied here is alpha-methylfentanyl. This group contains a substitution similar to the 3-methylfentanyl that was examined in the previous example on the previous image in this series (Fentanyl Synthesis p4.png), but it is on the phenethyl chain as opposed to being implanted on the piperidine ring. We then mark the two stereocenters, one on the C-4 carbon just as on fentanyl itself, and

1482-731: The α-methyl group interferes with binding to metabolic enzymes which break the drug down. Since fentanyl itself is highly potent and notorious for causing fatal overdoses when abused, and also very short lasting with recreational users often administering doses every hour, α-methylfentanyl could have several advantages over the parent compound as a recreational drug. Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching , nausea and potentially serious respiratory depression (namely with overdoses or improper drug-combinations, such as with benzodiazepines ) which can be life-threatening. Fentanyl analogs such as α-methylfentanyl and 3-methylfentanyl are often used as

1521-502: Was extended through December 31, 2024 by Public Law 117-328. Several jurisdictions have implemented analogue law controls of fentanyl analogues in an attempt to pre-emptively ban novel derivatives before they appear on the market. One representative example is the New Zealand provisions enacted in 1988 in response to the first wave of fentanyl derivatives. This bans a set of structures as follows; "Fentanyl analogues, in which

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