Skip to main content
SpringerLink
Log in

Pathological Effects and Adverse Events Associated with the Phenylethylamine Derivative NBOMe

A Focus on Limb Ischemia

  • Reference work entry
  • First Online:
Handbook of Substance Misuse and Addictions

  • 63 Accesses

Abstract

The abuse of new psychoactive substances (NPS) is increasingly rising to a global issue exposing especially young healthy persons to serious, in many cases life-threatening complications. N-benzylphenethylamines (NBOMes) are potent agonists of the serotonin receptor 5-HT2A and were initially developed for research purposes. The side effects in consumers comprise a clinical appearance similar to the effects of intake of other drugs such as cocaine, amphetamines, or tetrahydrocannabinol, the most serious being vasoconstriction, hemostasis, thrombosis, ischemia, seizures, hyperthermia, and rhabdomyolysis. Patients often present to the clinical ward with severe limb or cardiac ischemia. Rapid clinical diagnosis and appropriate therapy is crucial for muscle/ limb salvage. However, long-term patient outcome is determined to a great extent by the cessation of drug abuse.

The following chapter aims at raising awareness on serious side effects of NBOMes affecting the vascular system, of which the consumers are mostly unconscious.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 1,999.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 549.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Abbreviations

ADP:

Adenosine diphosphate

DSA:

Digital subtraction angiography

IP3:

Inositol 1,4,5-trisphosphate

LEAD:

Lower extremity artery disease

NBOMe:

N-benzylphenethylamine

NPS:

New psychoactive substances

PAD:

Peripheral artery disease

PLC:

Phospholipase C

5-HT:

5- hydroxytryptamine

References

  • Akasaki Y, Ohishi M (2020) Cerebrovascular and cardiovascular diseases caused by drugs of abuse. Hypertens Res 43:363–371

    Article  Google Scholar 

  • Al-Imam A (2018) 25b-NBOMe: a case report of sudden death and insightful view of Google trends data. Iran J Psychiatry Behav Sci 12(1):e9870

    Article  Google Scholar 

  • Anzenberger J, Klein C (2019) Comparison between drug-related deaths data from special and general mortality registers in Austria. Implications for monitoring and policy making. Lisbon Addictions 2019, 23. Oktober 2019, Lissabon

    Google Scholar 

  • Anzenberger J, Busch M, Gaiswinkler S, Grabenhofer-Eggerth A, Klein C, Schmutterer I et al (2020) Epidemiologiebericht Sucht 2020. Illegale Drogen, Alkohol und Tabak. Gesundheit Ă–sterreich, Wien

    Google Scholar 

  • Bostwick DG (1981) Amphetamine induced cerebral vasculitis. Hum Pathol 12:1031–1033

    Article  CAS  Google Scholar 

  • Braden MR, Parrish JC, Naylor JC, Nichols DE (2006) Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists. Mol Pharmacol 70:1956–1964

    Article  CAS  Google Scholar 

  • Brennan TV, Lin L, Huang X, Cardona DM, Li Z, Dredge K et al (2012) Heparan sulfate, an endogenous TLR4 agonist, promotes acute GVHD after allogeneic stem cell transplantation. Blood 120:2899–2908

    Article  CAS  Google Scholar 

  • Broadley KJ (2010) The vascular effects of trace amines and amphetamines. Pharmacol Ther 125:363–375

    Article  CAS  Google Scholar 

  • Carhart-Harris R, Giribaldi B, Watts R, Baker-Jones M, Murphy-Beiner A, Murphy R et al (2021) Trial of psilocybin versus escitalopram for depression. N Engl J Med 384:1402–1411

    Article  CAS  Google Scholar 

  • Crandall CG, Vongpatanasin W, Victor RG (2002) Mechanism of cocaine-induced hyperthermia in humans. Ann Intern Med 136:785–791

    Article  CAS  Google Scholar 

  • Dyer DC, Gant DW (1973) Vasoconstriction produced by hallucinogens on isolated human and sheep umbilical vasculature. J Pharmacol Exp Ther 184:366

    CAS  PubMed  Google Scholar 

  • el-Mahdy SA. 5-Hydroxytryptamine (serotonin) enhances ventricular arrhythmias induced by acute coronary artery ligation in rats

    Google Scholar 

  • Ertl S, Stastka L, Löffler-Stastka H (2020) Strukturiertes fallorientiertes Lernen. psychopraxis neuropraxis 23:240–245

    Article  Google Scholar 

  • Franklin JM, Carrasco GA (2015) Cocaine potentiates multiple 5-HT2A receptor signaling pathways and is associated with decreased phosphorylation of 5-HT2A receptors in vivo. J Mol Neurosci 55:770–777

    Article  CAS  Google Scholar 

  • Fujita M, Minamino T, Sanada S, Asanuma H, Hirata A, Ogita H, Okada K-I, Tsukamoto O, Takashima S, Tomoike H, Node K, Hori M, Kitakaze M (2004) Selective blockade of serotonin 5-HT2A receptor increases coronary blood flow via augmented cardiac nitric oxide release through 5-HT1B receptor in hypoperfused canine hearts. J Mol Cell Cardiol 37:1219–1223. https://doi.org/10.1016/j.yjmcc.2004.09.016

  • Gong H, Nakamura T, Hattori K, Ohnuki T, Rashid M, Nakazawa M et al (2000) A novel 5-HT2 antagonist, sarpogrelate hydrochloride, shows inhibitory effects on both contraction and relaxation mediated by 5-HT receptor subtypes in porcine coronary arteries. Pharmacology 61:263–268

    Article  CAS  Google Scholar 

  • Gremmel T, Frelinger AL 3rd, Michelson AD (2016) Platelet physiology. Semin Thromb Hemost 42:191–204

    Article  CAS  Google Scholar 

  • Halberstadt AL (2017) Pharmacology and toxicology of N-Benzylphenethylamine (“NBOMe”) hallucinogens. In: Baumann MH, Glennon RA, Wiley JL (eds) Neuropharmacology of new psychoactive substances (NPS): the science behind the headlines. Springer International Publishing, Cham, pp 283–311

    Chapter  Google Scholar 

  • Halberstadt AL, Geyer MA (2014) Effects of the hallucinogen 2,5-dimethoxy-4-iodophenethylamine (2C-I) and superpotent N-benzyl derivatives on the head twitch response. Neuropharmacology 77:200–207

    Article  CAS  Google Scholar 

  • Heesch CM, Wilhelm CR, Ristich J, Adnane J, Bontempo FA, Wagner WR (2000) Cocaine activates platelets and increases the formation of circulating platelet containing microaggregates in humans. Heart 83:688–695

    Article  CAS  Google Scholar 

  • Hofmann GA, Zierfuss B, Koppensteiner R, Willfort-Ehringer A, Kopp C (2021) Thromboangiitis obliterans biomarker shifts in different acute phase stages: a case study. Ann Vasc Surg 73:509.e5–509.e9

    Article  Google Scholar 

  • https://gesundheitsziele-oesterreich.at/links-publikationen-english/. Retrieved on 15.06.2021

  • https://www.euro.who.int/__data/assets/pdf_file/0006/315852/Policy-Brief-19-Investing-health-literacy.pdf. Retrieved on 15.06.2021

  • https://www.nytimes.com/2021/05/09/health/psychedelics-mdma-psilocybin-molly-mental-health.html?searchResultPosition=1. Retrieved on 24.05.2021

  • Kosten TR, Tucker K, Gottschalk PC, Rinder CS, Rinder HM (2004) Platelet abnormalities associated with cerebral perfusion defects in cocaine dependence. Biol Psychiatry 55:91–97

    Article  CAS  Google Scholar 

  • Krendel DA, Ditter SM, Frankel MR, Ross WK (1990) Biopsy-proven cerebral vasculitis associated with cocaine abuse. Neurology 40:1092–1094

    Article  CAS  Google Scholar 

  • LĂłpez-GimĂ©nez JF, González-Maeso J (2018) Hallucinogens and serotonin 5-HT(2A) receptor-mediated signaling pathways. Curr Top Behav Neurosci 36:45–73

    Article  Google Scholar 

  • Masashi F, Tetsuo M, Shoji S, Hiroshi A, Akio H, Hisakazu O, Ken-ichiro O, Osamu T, Seiji T, Hitonobu T, Koichi N, Masatsugu H, Masafumi K (2004) Selective blockade of serotonin 5-HT2A receptor increases coronary blood flow via augmented cardiac nitric oxide release through 5-HT1B receptor in hypoperfused canine hearts, J Mol Cell Cardiol 37:1219–1223 https://doi.org/10.1016/j.yjmcc.2004.09.016

  • McDaid J, Docherty JR (2001) Vascular actions of MDMA involve α1 and α2-adrenoceptors in the anaesthetized rat. Br J Pharmacol 133:429–437

    Article  CAS  Google Scholar 

  • McKune CM, Watts SW (2001) Characterization of the serotonin receptor mediating contraction in the mouse thoracic aorta and signal pathway coupling. J Pharmacol Exp Ther 297:88

    CAS  PubMed  Google Scholar 

  • Mitchell JM, Bogenschutz M, Lilienstein A, Harrison C, Kleiman S, Parker-Guilbert K et al (2021) MDMA-assisted therapy for severe PTSD: a randomized, double-blind, placebo-controlled phase 3 study. Nat Med 27:1025–1033

    Article  CAS  Google Scholar 

  • Nagatomo T, Rashid M, Abul Muntasir H, Komiyama T (2004) Functions of 5-HT2A receptor and its antagonists in the cardiovascular system. Pharmacol Ther 104:59–81

    Article  CAS  Google Scholar 

  • Nakamura M, Shintani-Ishida K, Ikegaya H (2018) 5-HT2A receptor agonist-induced hyperthermia is induced via vasoconstriction by peripheral 5-HT2A receptors and brown adipose tissue thermogenesis by peripheral serotonin loss at a high ambient temperature. J Pharmacol Exp Ther 367:356

    Article  CAS  Google Scholar 

  • Nichols DE, Sassano MF, Halberstadt AL, Klein LM, Brandt SD, Elliott SP et al (2015) N-Benzyl-5-methoxytryptamines as potent serotonin 5-HT2 receptor family agonists and comparison with a series of phenethylamine analogues. ACS Chem Neurosci 6:1165–1175

    Article  CAS  Google Scholar 

  • Nitanda A, Yasunami N, Tokumo K, Fujii H, Hirai T, Nishio H (2005) Contribution of the peripheral 5-HT2A receptor to mechanical hyperalgesia in a rat model of neuropathic pain. Neurochem Int 47:394–400

    Article  CAS  Google Scholar 

  • Offermanns S (2006) Activation of platelet function through G protein–coupled receptors. Circ Res 99:1293–1304

    Article  CAS  Google Scholar 

  • Pertz H, Elz S (1995) In-vitro pharmacology of sarpogrelate and the enantiomers of its major metabolite: 5-HT2A receptor specificity, stereoselectivity and modulation of ritanserin-induced depression of 5-HT contractions in rat tail artery. J Pharm Pharmacol 47:310–316

    Article  CAS  Google Scholar 

  • Rapoport RM, Yoon S, Zuccarello M (2016) Cocaine constrictor mechanisms of the cerebral vasculature. J Cardiovasc Pharmacol 67

    Google Scholar 

  • Reece AS, Norman A, Hulse GK (2017) Acceleration of cardiovascular-biological age by amphetamine exposure is a power function of chronological age. Heart Asia 9:30–38

    Article  Google Scholar 

  • Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI et al (2001) Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin. Synapse 39:32–41

    Article  CAS  Google Scholar 

  • Saxena PR, VillalĂłn CM (1990) Cardiovascular effects of serotonin agonists and antagonists. J Cardiovasc Pharmacol 15:S17–S34

    Article  CAS  Google Scholar 

  • Siniscalchi A, Bonci A, Mercuri NB, De Siena A, De Sarro G, Malferrari G et al (2015) Cocaine dependence and stroke: pathogenesis and management. Curr Neurovasc Res 12:163–172

    Article  CAS  Google Scholar 

  • Suhrcke M, de Paz Nieves C (2011) The impact of health and health behaviours on educational outcomes in high-income countries: a review of the evidence. WHO Regional Office for Europe, Copenhagen. Retrieved on 11.06.2021

    Google Scholar 

  • Suzuki J, Dekker MA, Valenti ES, Arbelo Cruz FA, Correa AM, Poklis JL et al (2015) Toxicities associated with NBOMe ingestion-a novel class of potent hallucinogens: a review of the literature. Psychosomatics 56:129–139

    Article  Google Scholar 

  • Treadwell SD, Robinson TG (2007) Cocaine use and stroke. Postgrad Med J 83:389–394

    Article  CAS  Google Scholar 

  • VillalĂłn CM, CenturiĂłn D (2007) Cardiovascular responses produced by 5-hydroxytriptamine:a pharmacological update on the receptors/mechanisms involved and therapeutic implications. Naunyn Schmiedeberg's Arch Pharmacol 376:45–63

    Article  Google Scholar 

  • Wadowski PP, Giurgea GA, Schlager O, Luf A, Gremmel T, Hobl EL et al (2019) Acute limb ischemia after intake of the phenylethylamine derivate NBOMe. Int J Environ Res Public Health 16:5071

    Article  Google Scholar 

  • Wang Y, Park SY, Oh KH, Min Y, Lee Y-J, Lee S-Y et al (2011) Characteristics of 5-hydroxytryptamine receptors involved in contraction of feline ileal longitudinal smooth muscle. Korean J Physiol Pharmacol 15:267–272

    Article  CAS  Google Scholar 

  • Welsh DJ, Harnett M, MacLean M, Peacock AJ (2004) Proliferation and signaling in fibroblasts. Am J Respir Crit Care Med 170:252–259

    Article  Google Scholar 

  • Westover AN, McBride S, Haley RW (2007) Stroke in young adults who abuse amphetamines or cocaine: a population-based study of hospitalized patients. Arch Gen Psychiatry 64:495–502

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Internal Medicine II, Division of Angiology, Medical University of Vienna, Vienna, Austria

    Patricia Pia Wadowski & Renate Koppensteiner

  2. Department of Psychoanalysis and Psychotherapy, Medical University of Vienna, Vienna, Austria

    Henriette Löffler-Stastka

Authors
  1. Patricia Pia Wadowski
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Henriette Löffler-Stastka
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Renate Koppensteiner
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Patricia Pia Wadowski .

Editor information

Editors and Affiliations

  1. School of Life Sciences, University of Westminster, London, UK

    Vinood B. Patel

  2. School of Life Course and Population Sciences, Faculty of Life Sciences and Medicine, King’s College London, London, UK

    Victor R. Preedy

Rights and permissions

Reprints and permissions

Copyright information

© 2022 Springer Nature Switzerland AG

About this entry

Check for updates. Verify currency and authenticity via CrossMark

Cite this entry

Wadowski, P.P., Löffler-Stastka, H., Koppensteiner, R. (2022). Pathological Effects and Adverse Events Associated with the Phenylethylamine Derivative NBOMe. In: Patel, V.B., Preedy, V.R. (eds) Handbook of Substance Misuse and Addictions. Springer, Cham. https://doi.org/10.1007/978-3-030-92392-1_165

Download citation

Publish with us

Policies and ethics

Search

Navigation