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How Fentanyl Laid Waste to Opium Trade

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发表于 5-7-2024 14:52:52 | 显示全部楼层 |阅读模式
Simon Romero, How Fentanyl Laid Waste to Guatemala's Time-Worn Trade in Opium . New York Times, Apr 29, 2024, at page A9.
https://www.nytimes.com/2024/04/ ... yl-opium-poppy.html
("In the United States, the world’s largest market for illicit drugs, fentanyl has largely displaced heroin because of how cheaply and easily Mexican cartels can produce the synthetic opioid in makeshift labs using chemicals from China. Fentanyl is so potent that it can be smuggled in small quantities hidden in vehicles, another advantage over heroin")

My comment: I am interested in chemistry and pharmacology, so I stop reading when reaching the quotation.
(a) morphine
https://en.wikipedia.org/wiki/Morphine
("is found naturally in opium, a dark brown resin produced by drying the latex of opium poppies (Papaver somniferum). It is mainly used as an analgesic (pain medication). * * * Morphine is the principal alkaloid in raw opium and constitutes roughly 8–19% of opium by dry weight (depending on growing conditions) [view the pie chart with the caption: 'First generation production of alkaloids from licit latex-derived opium']. * * * [section 10 History:] possible references to morphine may go as far back as 2100 BC as Sumerian clay tablets * * * Morphine was discovered as the first active alkaloid extracted from the opium poppy plant in December 1804 in Paderborn[, in present-day Germany] by German pharmacist Friedrich Sertürner. * * * Sertürner originally named the substance morphium after the Greek god of dreams, Morpheus, as it has a tendency to cause sleep. Sertürner's morphium was six times stronger than opium [likely because morphine is more concentrated; after all, morphine constituted half of opium chemicals]")
(b)
(i) heroin
https://en.wikipedia.org/wiki/Heroin

section 6 Chemistry: Heroin "is produced from acetylation of morphine

section 7 History: "The opium poppy was cultivated in lower Mesopotamia as long ago as 3400 BC. * * * [Heroin] was first synthesized in 1874 by CR Alder Wright, an English chemist working at St Mary's Hospital Medical School in London * * * The head of Bayer's research department reputedly coined the drug's new name of 'heroin,' based on the German heroisch which means 'heroic, strong' (from the ancient Greek word 'heros, ήρως' * * * [heroin is] one and a half to two times more potent than morphine itself).

(ii) Regarding section 6 immediately above. The acetylation is the only difference between morphine and heroin. Compare the chemical structures of these two shows that at both 7 and 11 o'clock positions, heroin has CH3CO- that morphine does not have.
Acetic acid CH3COO-H reacts with the two hydroxyl group (-OH, a distinguishing mark of alcohol when a carbon atom -- as opposed to a sodium ion in NaOH -- connects a hydroxyl group), to create ester bonds -CO-O-R at these two positions.
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 楼主| 发表于 5-7-2024 14:54:03 | 显示全部楼层
(1)
(a) Fentanyl "is 20 to 40 times more potent than heroin."  en.wikipedia.org for fentanyl.
(b) oxycodone
https://en.wikipedia.org/wiki/Oxycodone
("OxyContin (which is the extended [or controlled] release form [of oxycodone]), is a semi-synthetic opioid")
is similar to morphine in chemical structure.

(2)
(a) opioid receptor
https://en.wikipedia.org/wiki/Opioid_receptor
("The [opioid] receptors were named using the first letter of the first ligand that was found to bind to them. Morphine was the first chemical shown to bind to 'mu' receptors [also known as MOR, where OR is opioid receptor]. The first letter of the drug morphine is m, rendered as the corresponding Greek letter μ")

Morphine, heroin, oxycontin, and fentanyl all acts on MOR.
(b) There are endogenous opioid peptides (which brain itself makes).
https://en.wikipedia.org/wiki/Opioid_peptide
("The effects of these peptides vary, but they all resemble those of opiates")
(c) So far, scientists have not been able to discover an opioid that kills pain but at the same time is nonadditive. But recently, Mei-Chuan Ko, PhD, professor at Wake Forest University School of Medicine, found one: AT-121.

(3)  
(a) Christopher Cavacuiti, Chapter 8 The Pharmacology of Opioids. In Robeck I et al (eds), The American Society of Addiction Medicine Handbook on Pain and Addiction The American Society of Addiction Medicine Handbook on Pain and Addiction. Oxford University Press, 2018
https://academic.oup.com/book/25285/chapter-abstract/191484262
("Opioid can be divided ito five chemical classes: phenanthrenes, benzomorphans, phenylpiperidines, diphenylheptanes, and phenylpropanolamines. * * * The prototypical class of opioids, encompassing morphine-, heroin- is the phenanthrene class. * * * Fantanyl * * * belong to phenylpiperidine class of opioids)

If one clicks the URL, there will be no access. If one instead google the author and chapter title, there will be. But there is no need to read the rest of this chapter, other than the quotation.
(b) Theodore H Stanley, The Fentanyl Story. Journal of Pain, 15: 1215 (2014).
https://www.jpain.org/article/S1526-5900(14)00905-5/pdf

You may click the pdf format at the upper right corner of this Web page.

Read pages 1-2 only: Fentanyl "was first synthesized by [Belgian physician] Dr Paul Janssen and his firm] the Janssen Company of Beerse, Belgium,
in December 1960. * * * Dr. Janssen and his colleagues in his company believed that the piperidine ring (Fig 2), present in both morphine and meperidine, was the most important chemical structure that produced analgesia in these molecules. They began working with meperidine, rather than morphine, as the parent molecule in the production of newer and better compounds because it was much less complex a molecule and thus easier to manipulate. * * * The Janssen research team realized that both morphine and meperidine were poor and slow-onset analgesics because they could not easily penetrate into the central nervous system. Therefore, they concluded that they needed to synthesize more fat-soluble derivatives." (After all, brain is laden with fat -- just not the kind of fat in adipose tissue.)

(4)
(a) In Fig 2, Notice one of the differences between meperidine and piperidine is that at the 9 o'clock position, the former has methyl group and the latter has a hydrogen atom. Another difference is that meperidine has an al phenyl group.
https://en.wikipedia.org/wiki/Phenyl_group
(section 1 Nomenclature, section 1.1 Etymology)
(b) English dictionary:
* fentanyl (etymology)
https://en.wiktionary.org/wiki/fentanyl
* meperidine (etymology)
https://en.wiktionary.org/wiki/meperidine
(c) For meperidine, see pethidine
https://en.wikipedia.org/wiki/Pethidine
("also known as meperidine and sold under the brand name Demerol among others, is a fully synthetic opioid pain medication of the phenylpiperidine class. Synthesized in 1938 as a potential anticholinergic agent by the German chemist Otto Eisleb, its analgesic properties were first recognized by Otto Schaumann while working for IG Farben, in Germany")

So, meperidine was discovered in another pursuit but repurposed later -- the same as viagra.
(d) piperidine
https://en.wikipedia.org/wiki/Piperidine
(section 1 Production: name)
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 楼主| 发表于 5-7-2024 14:54:30 | 显示全部楼层
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The convoy rolled out of the military base before dawn into the mist-shrouded mountains straddling Guatemala’s border with Mexico. Its mission: destroy opium poppies used to make heroin.

Armed with rifles and machetes, the caravan’s nearly 300 soldiers and police officers from elite counternarcotics units scaled steep hillsides and waded through bone-chilling streams. They chased leads from drone pilots and inhaled dust as they rode in the back of pickup trucks barreling down washboard dirt roads.

But after scouring village after village, they found only tiny plots of poppies here and there — a fraction of the region’s cultivation in previous years.

“The land here used to be covered in poppies,” said Ludvin López, a police commander, as soldiers fanned out around Ixchiguán, an area of remote hamlets populated by speakers of Mam, a Mayan language. But that was before opium prices plunged from $64 an ounce to about $9.60, he added.

The largely fruitless search for opium poppies in Guatemala over several days in March laid bare a seismic shift in Latin America’s drug trade.

In the United States, the world’s largest market for illicit drugs, fentanyl has largely displaced heroin because of how cheaply and easily Mexican cartels can produce the synthetic opioid in makeshift labs using chemicals from China. Fentanyl is so potent that it can be smuggled in small quantities hidden in vehicles, another advantage over heroin.

As a result, demand for opium poppies has plunged.

In Guatemala, poppy farmers are losing their primary income from what had been their only cash crop, forcing many in already poverty-stricken areas to migrate to the United States. At the same time, local and international authorities fear that Guatemala could emerge as a new hub for trading in the chemicals used to make fentanyl.

Drug busts along the United States-Mexico border also showcase heroin’s decline. In the 2023 fiscal year, U.S. Customs and Border Protection’s Office of Field Operations seized 1,500 pounds of heroin, down from 5,400 pounds in 2021.

Even as fentanyl lays waste to the heroin trade and counternarcotics priorities shift, American authorities say that U.S. support for poppy eradication efforts, though limited, is still needed in Guatemala to counter the reach of Mexican cartels that produce heroin.

Still, the highest priority in Guatemala now is combating synthetic drugs and the detection of precursor chemicals used to make fentanyl, said a State Department official who was not authorized to be identified discussing drug interdiction strategies.

But the soldiers stomping through small vegetable gardens in remote villages were after opium poppies. Finding a few poppies, in patches no bigger than a hopscotch area, they went to work with machetes, chopping the plants. They did the same to the occasional cannabis plant, which remains illegal to grow in Guatemala.

Multiple signs of United States support for the mission — and for Guatemala’s counternarcotics efforts in general — were on display. Some police officers on the mission belonged to units supported by the U.S. Drug Enforcement Administration and undergo regular polygraph and drug testing. Soldiers traveled in four-wheel-drive vehicles donated by the United States.

The State Department declined to provide a detailed breakdown of U.S. counternarcotics funding. But altogether, the country has recently received about $10 million to $20 million a year in military and police aid from the United States, according to Adam Isacson, the director of defense oversight at the Washington Office on Latin America, a research group.

That is roughly the same amount of such aid as a decade ago; overall, Guatemala ranks among the largest recipients of United States foreign assistance in Latin America.

An observer from the State Department, which has funded everything in Guatemala from training border police to an elite anti-gang unit, also accompanied the mission. He declined to comment, saying he wasn’t authorized to speak with journalists.

Since the soldiers’ efforts were mostly fruitless, they spent some of their time cracking jokes while mingling around their pickup trucks. Trying to spread good will, some distributed items from their food packets to villagers; others gave away cheap plastic toys to children.

Still, in an exceptionally poor region where each mature opium poppy plant is worth about 25 quetzals (about $3.20), some villagers clearly seethed at the soldiers’ presence. Some refused to talk to anyone in the convoy, which they viewed as removing one of their only sources of income.

“We hardly have any poppies left around here anymore,” said Ana Leticia Morales, 26, a Mam-speaking mother of two who makes a living selling gasoline smuggled from Mexico. “But the soldiers still come, not to help us, but to make things worse.”

Tensions around eradication efforts have flared for decades in Guatemala, Central America’s most populous country. Opium poppies, which were traditionally grown in mountainous regions stretching from Turkey to Pakistan, began appearing decades ago in Guatemala, as well as in parts of Mexico and Colombia.

Mexican cartels relied on Guatemalan farmers to grow the poppies and then turn them into opium gum. Smuggled across the border into Mexico, the cartels would transform the gum into heroin.

The United States initially responded by spraying herbicides from planes in Guatemala, but suspended those efforts after flight crews came under concentrated gunfire. This opened the way for the ground operations practiced today.

Fentanyl’s emergence over the last decade as a cheaper and much more profitable source of income for the cartels upended the poppy trade in Mexico while producing spillover effects in Central America. Now, the cartels don’t need to worry about heavy rains, which can destroy harvests. They also don’t need to worry about eradication operations.

Eradicators in Guatemala destroyed about 2,011 acres of opium poppies in 2017 compared with just seven acres in 2023, Guatemalan government figures show.

The decline speaks to the ease in Mexico of using chemicals imported from China to produce fentanyl in small labs about the size of a studio apartment, making it ideal for being manufactured in urban settings.

“It’s easier to produce a synthetic opioid in a laboratory than relying on a crop grown in remote mountains,” said Rigoberto Quemé, an anthropologist from the poppy-growing region of Guatemala. “The authorities are attacking the weakest link in the production chain,” he added, referring to eradication efforts. “But instead of disappearing, drug trafficking is still growing exponentially.”

Guatemala, in fact, remains a crucial smuggling nexus for yet another illicit drug — cocaine. The country is also emerging as a place where coca, the plant used to make cocaine, is grown.

Counternarcotics officials in Guatemala, Mexico and the United States worry that Sinaloa and Jalisco New Generation, the two Mexican cartels vying for control of the routes already used for smuggling cocaine and opium gum from Guatemala, could use those same passages for transporting fentanyl chemical precursors into Mexico.

The Guatemalan authorities last year arrested Ana Gabriela Rubio Zea, an entrepreneur known for flaunting her wealth on social media, in connection to a scheme to import chemicals from China to manufacture fentanyl for Mexico’s Sinaloa Cartel.

Ms. Rubio Zea, who ran an upscale clothing boutique in the elite stronghold of Cayalá in Guatemala City, was extradited to the United States last July to face fentanyl distribution and money laundering charges that could result in life in prison. The Mexican authorities followed that move with an arrest in January of Jason Antonio Yang López, a Guatemalan businessman subjected to sanctions by the U.S. Treasury for importing fentanyl precursor chemicals.

Guatemala’s new president, Bernardo Arévalo, is strengthening ties with the United States in a bid to respond to the fentanyl trade. In a ceremony in March attended by American officials, his government said it was trying to improve ways to combat the trade in precursor chemicals in Guatemala.

But such efforts mean little for villagers confronting fading demand for poppies on the one hand, and eradication programs on the other.

Regino García, a Mam leader from San Antonio Ixchiguán, said poppy prices began tumbling in 2017, eventually crashing to 2,000 quetzals ($256) per kilo from 18,000 quetzals ($2,310).

“Poppies used to help a lot of people make ends meet,” Mr. García said. Now, he said, the steep decline in poppy prices inflicted so much economic pain that “before the money runs out, people depart for the United States.”
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