Not to be confused with
hyoscine , another name for the drug scopolamine.
Tropane alkaloid
Hyoscyamine
Trade names Anaspaz, Levbid, Levsin
AHFS /
Drugs.com
Monograph
MedlinePlus
a684010
Routes of administration
By mouth , Injection
ATC code
Legal status
Bioavailability 50% protein binding
Metabolism
Liver
Elimination half-life 3–5 hrs.
Excretion
Kidney
(S )-(1R ,3r ,5S )-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
CAS Number
PubChem
CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (
EPA )
ECHA InfoCard
100.002.667
Formula C 17 H 23 N O 3
Molar mass 289.375 g·mol−1 3D model (
JSmol )
CN3[C@H]1CC[C@@H]3C[C@@H](C1)OC(=O)[C@H](CO)c2ccccc2
InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16-/m1/s1
Y Key:RKUNBYITZUJHSG-FXUDXRNXSA-N
Y
N Y
(what is this?)
(verify)
Hyoscyamine (also known as daturine or duboisine ) is a naturally occurring
tropane alkaloid and plant toxin. It is a
secondary metabolite found in certain plants of the family
Solanaceae , including
henbane ,
mandrake ,
angel's trumpets ,
jimsonweed ,
the sorcerers' tree , and
Atropa belladonna (deadly nightshade). It is the
levorotary
isomer of
atropine (third of the three major nightshade alkaloids) and thus sometimes known as levo-atropine.
[1]
In 2021, it was the 272nd most commonly prescribed medication in the United States, with more than 900,000 prescriptions.
[2]
[3]
Hyoscyamine is used to provide symptomatic relief of spasms caused by various lower abdominal and bladder disorders including
peptic ulcers ,
irritable bowel syndrome ,
diverticulitis ,
pancreatitis ,
colic , and
interstitial cystitis .
[4]
[5]
[6] It has also been used to relieve some heart problems, control some of the symptoms of
Parkinson's disease , as well as for control of abnormal respiratory symptoms and "hyper-mucus secretions" in patients with lung disease.
[7]
The ingredients of this
Clap Mixture are sodium citrate, sodium bicarbonate, liquid extract of hyoscyamine and chloroform dissolved in water.
It is also useful in pain control for neuropathic pain, chronic pain and palliative care — "comfort care" — for those with intractable pain from treatment resistant, untreatable, and incurable diseases. When combined with opioids it increases the level of analgesia (pain relief) obtained.
[8] Several mechanisms are thought to contribute to this effect. The closely related drugs atropine and
hyoscine and other members of the anticholinergic drug group like
cyclobenzaprine ,
trihexyphenidyl , and
orphenadrine are also used for this purpose.
[9] When hyoscyamine is used along with opioids or other anti-peristaltic agents, measures to prevent constipation are especially important given the risk of paralytic
ileus .
[10]
Side effects include dry mouth and throat, increased appetite leading to weight gain, eye pain, blurred vision, restlessness, dizziness,
arrhythmia , flushing, and faintness.
[5] An overdose will cause headache, nausea, vomiting, and central nervous system symptoms including disorientation, hallucinations, euphoria, sexual arousal, short-term memory loss, and possible coma in extreme cases. The euphoric and sexual effects are stronger than those of atropine but weaker than those of
hyoscine , as well as
dicycloverine ,
orphenadrine ,
cyclobenzaprine ,
trihexyphenidyl , and ethanolamine antihistamines like
phenyltoloxamine .
[11]
[12]
Hyoscyamine is an
antimuscarinic ; i.e., an antagonist of
muscarinic acetylcholine receptors . It blocks the action of
acetylcholine at sweat glands (sympathetic) and at
parasympathetic sites in salivary glands, stomach secretions, heart muscle,
sinoatrial node , smooth muscle in the
gastrointestinal tract , and the
central nervous system . It increases cardiac output and heart rate, lowers blood pressure and dries secretions.
[13] It may antagonize
serotonin .
[14] At comparable doses, hyoscyamine has 98 percent of the
anticholinergic power of atropine. The other major
Atropa belladonna -derived drug
hyoscine (known in the United States as Scopolamine) has 92 per cent of the antimuscarinic potency of atropine.
[14]
Biochemistry of tropane class compounds. Hyoscyamine and
scopolamine are present and labeled in the diagram.
Hyoscyamine can be extracted from plants of the family
Solanaceae , notably
Datura stramonium . As hyoscyamine is a direct
precursor in the
plant biosynthesis of hyoscine , it is produced via the same
metabolic pathway .
[15]
The
biosynthesis of hyoscine begins with the
decarboxylation of L -
ornithine to
putrescine by
ornithine decarboxylase (
EC 4.1.1.17 ). Putrescine is
methylated to N -methylputrescine by
putrescine N -methyltransferase (
EC 2.1.1.53 ).
[15]
A
putrescine oxidase (
EC 1.4.3.10 ) that specifically recognizes methylated putrescine catalyzes the
deamination of this compound to 4-methylaminobutanal which then undergoes a spontaneous ring formation to N -methylpyrrolium cation. In the next step, the pyrrolium cation condenses with
acetoacetic acid yielding
hygrine . No enzymatic activity could be demonstrated that catalyzes this reaction. Hygrine further rearranges to
tropinone .
[15]
Subsequently,
tropinone reductase I (
EC 1.1.1.206 ) converts tropinone to
tropine which condenses with
phenylalanine -derived phenyllactate to littorine. A
cytochrome P450 classified as Cyp80F1
[16] oxidizes and rearranges littorine to hyoscyamine
aldehyde .
A
bush medicine developed by
Aboriginal peoples of the
eastern states of Australia from the soft
corkwood tree, or
Duboisia myoporoides , was used by the
Allies in World War II to stop soldiers getting
seasick when they sailed across the
English Channel during the
Invasion of Normandy . Later, it was found that the same substance could be used in the production of
scopolamine and hyoscyamine, which are used in
eye surgery , and a multi-million dollar industry was built in
Queensland based on this substance.
[17]
Brand names for hyoscyamine include Symax, HyoMax, Anaspaz, Egazil, Buwecon, Cystospaz, Levsin, Levbid, Levsinex, Donnamar, NuLev, Spacol T/S, and Neoquess.
[18]
^ Ushimaru R, Ruszczycky MW, Liu HW (January 2019).
"Changes in Regioselectivity of H Atom Abstraction during the Hydroxylation and Cyclization Reactions Catalyzed by Hyoscyamine 6β-Hydroxylase" . Journal of the American Chemical Society . 141 (2): 1062–1066.
doi :
10.1021/jacs.8b11585 .
PMC
6488026 .
PMID
30545219 .
^
"The Top 300 of 2021" . ClinCalc .
Archived from the original on 15 January 2024. Retrieved 14 January 2024 .
^
"Hyoscyamine - Drug Usage Statistics" . ClinCalc . Retrieved 14 January 2024 .
^ National Clinical Guideline Centre (UK) (2012).
Treatment to improve bladder storage . NBK132836 (8th ed.). United Kingdom:
Royal College of Physicians . p. 83 – via
National Library of Medicine .
^
a
b
"Hyoscyamine Uses, Side Effects & Warnings" .
Drugs.com .
Archived from the original on 20 August 2022. Retrieved 20 August 2022 .
^
"Bladder Control Medicines | NIDDK" .
National Institute of Diabetes and Digestive and Kidney Diseases .
Archived from the original on 20 August 2022. Retrieved 20 August 2022 .
^
"Hyoscyamine: MedlinePlus Drug Information" .
medlineplus.gov .
Archived from the original on 20 August 2022. Retrieved 20 August 2022 .
^ Harden RN (March 2005). "Chronic neuropathic pain. Mechanisms, diagnosis, and treatment". The Neurologist . 11 (2): 111–122.
doi :
10.1097/01.nrl.0000155180.60057.8e .
PMID
15733333 .
S2CID
12602416 .
^ Ali-Melkkilä T, Kanto J, Iisalo E (October 1993). "Pharmacokinetics and related pharmacodynamics of anticholinergic drugs". Acta Anaesthesiologica Scandinavica . 37 (7): 633–642.
doi :
10.1111/j.1399-6576.1993.tb03780.x .
PMID
8249551 .
S2CID
22808654 .
^ Kamimura A, Howard S, Weaver S, Panahi S, Ashby J (December 2020).
"The Use of Complementary and Alternative Medicine Strategies, Opioids, and Nonsteroidal Anti-Inflammatory Drugs (NSAIDS) Among Patients Attending a Free Clinic" . Journal of Patient Experience . 7 (6): 1701–1707.
doi :
10.1177/2374373520937514 .
PMC
7786764 .
PMID
33457633 .
^ Kang M, Galuska MA, Ghassemzadeh S (2022).
"Benzodiazepine Toxicity" . StatPearls . Treasure Island (FL): StatPearls Publishing.
PMID
29489152 . Archived from
the original on 20 August 2022.
^
"Hyoscyamine Sulfate Sublingual Tablets, 0.125 mgRx Only" . www.dailymed.nlm.nih.gov .
Archived from the original on 20 August 2022. Retrieved 20 August 2022 .
^ Edwards Pharmaceuticals, Inc., Belcher Pharmaceuticals, Inc. (May 2010).
"DailyMed" . U.S. National Library of Medicine. Retrieved 13 January 2013 .
^
a
b Kapoor AK, Raju SM (2013).
Illustrated Medical Pharmacology . JP Medical Ltd. p. 131.
ISBN
9789350906552 . Retrieved 11 January 2014 .
^
a
b
c Ziegler J, Facchini PJ (2008). "Alkaloid biosynthesis: metabolism and trafficking". Annual Review of Plant Biology . 59 (1): 735–769.
doi :
10.1146/annurev.arplant.59.032607.092730 .
PMID
18251710 .
^ Li R, Reed DW, Liu E, Nowak J, Pelcher LE, Page JE, et al. (May 2006).
"Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement" . Chemistry & Biology . 13 (5): 513–520.
doi :
10.1016/j.chembiol.2006.03.005 .
PMID
16720272 .
^
"Visitors to Art of Healing exhibition told how Australian Indigenous bush medicine was given to every allied soldier landing at Normandy on D-Day" . King's College London . 7 June 2019. Retrieved 2 June 2020 .
^
"Hyoscyamine - brand name list from Drugs.com" .
Drugs.com .
Archived from the original on 20 August 2022. Retrieved 20 August 2022 .
Plants / animals People Compounds
Psychedelics (
5-HT2A agonists)
Benzofurans
Lyserg‐ amides
Phenethyl‐ amines
2C-x
25x -NBx
25x -
NB 25x -
NB3OMe 25x -
NB4OMe 25x -
NBF 25x -
NBMD 25x -
NBOH 25x -
NBOMe Atypical structures
25x -NMx
N-(2C)-fentanyl
3C-x 4C-x
DOx HOT-x
MDxx Mescaline (subst.)
TMAs
TMA
TMA-2
TMA-3
TMA-4
TMA-5
TMA-6
Others
Piperazines
Tryptamines
alpha -alkyltryptamines x -
DALT x -
DET x -
DiPT x -
DMT
4,5-DHP-DMT
2,N,N-TMT
4-AcO-DMT
4-HO-5-MeO-DMT
4,N,N-TMT
4-Propionyloxy-DMT
5,6-diBr-DMT
5-AcO-DMT
5-Bromo-DMT
5-MeO-2,N ,N -TMT
5-MeO-4,N ,N -TMT
5-MeO-α,N,N-TMT
5-MeO-DMT
5-N ,N -TMT
7,N,N-TMT
α,N,N-TMT
(Bufotenin) 5-HO-DMT
DMT
Norbaeocystin
(Psilocin) 4-HO-DMT
(Psilocybin) 4-PO-DMT
x -
DPT Ibogaine-related x -
MET x -
MiPT Others
Others
Dissociatives (
NMDAR
antagonists )
Deliriants (
mAChR
antagonists ) Others
mAChRs Tooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
3-Quinuclidinyl benzilate
4-DAMP
Aclidinium bromide (
+formoterol )
Abediterol
AF-DX 250
AF-DX 384
Ambutonium bromide
Anisodamine
Anisodine
Antihistamines (first-generation) (e.g.,
brompheniramine ,
buclizine ,
captodiame ,
chlorphenamine (chlorpheniramine) ,
cinnarizine ,
clemastine ,
cyproheptadine ,
dimenhydrinate ,
dimetindene ,
diphenhydramine ,
doxylamine ,
meclizine ,
mequitazine ,
perlapine ,
phenindamine ,
pheniramine ,
phenyltoloxamine ,
promethazine ,
propiomazine ,
triprolidine )
AQ-RA 741
Atropine
Atropine methonitrate
Atypical antipsychotics (e.g.,
clozapine ,
fluperlapine ,
olanzapine (
+fluoxetine ),
rilapine ,
quetiapine ,
tenilapine ,
zotepine )
Benactyzine
Benzatropine (benztropine)
Benzilone
Benzilylcholine mustard
Benzydamine
Bevonium
BIBN 99
Biperiden
Bornaprine
Camylofin
CAR-226,086
CAR-301,060
CAR-302,196
CAR-302,282
CAR-302,368
CAR-302,537
CAR-302,668
Caramiphen
Cimetropium bromide
Clidinium bromide
Cloperastine
CS-27349
Cyclobenzaprine
Cyclopentolate
Darifenacin
DAU-5884
Desfesoterodine
Dexetimide
DIBD
Dicycloverine (dicyclomine)
Dihexyverine
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EA-3167
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Fenpiverinium
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+beclometasone/formoterol ,
+indacaterol ,
+neostigmine )
Hexahydrodifenidol
Hexahydrosiladifenidol
Hexbutinol
Hexocyclium
Himbacine
HL-031,120
Homatropine
Imidafenacin
Ipratropium bromide (
+salbutamol )
Isopropamide
J-104,129
Hyoscyamine
Mamba toxin 3
Mamba toxin 7
Mazaticol
Mebeverine
Meladrazine
Mepenzolate
Methantheline
Methoctramine
Methylatropine
Methylhomatropine
Methylscopolamine
Metixene
Muscarinic toxin 7
N-Ethyl-3-piperidyl benzilate
N-Methyl-3-piperidyl benzilate
Nefopam
Octatropine methylbromide (anisotropine methylbromide)
Orphenadrine
Otenzepad (AF-DX 116)
Otilonium bromide
Oxapium iodide
Oxitropium bromide
Oxybutynin
Oxyphencyclimine
Oxyphenonium bromide
PBID
PD-102,807
PD-0298029
Penthienate
Pethidine
pFHHSiD
Phenglutarimide
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Piperidolate
Pirenzepine
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Prifinium bromide
Procyclidine
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Propantheline bromide
Propiverine
Quinidine
3-Quinuclidinyl thiochromane-4-carboxylate
Revefenacin
Rociverine
RU-47,213
SCH-57,790
SCH-72,788
SCH-217,443
Scopolamine (hyoscine)
Scopolamine butylbromide (hyoscine butylbromide)
Silahexacyclium
Sofpironium bromide
Solifenacin
SSRIs Tooltip Selective serotonin reuptake inhibitors (e.g.,
femoxetine ,
paroxetine )
Telenzepine
Terodiline
Tetracyclic antidepressants (e.g.,
amoxapine ,
maprotiline ,
mianserin ,
mirtazapine )
Tiemonium iodide
Timepidium bromide
Tiotropium bromide
Tiquizium bromide
Tofenacin
Tolterodine
Tricyclic antidepressants (e.g.,
amitriptyline (
+perphenazine ),
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butriptyline ,
cidoxepin ,
clomipramine ,
desipramine ,
desmethyldesipramine ,
dibenzepin ,
dosulepin (dothiepin) ,
doxepin ,
imipramine ,
lofepramine ,
nitroxazepine ,
northiaden (desmethyldosulepin) ,
nortriptyline ,
protriptyline ,
quinupramine ,
trimipramine )
Tridihexethyl
Trihexyphenidyl
Trimebutine
Tripitamine (tripitramine)
Tropacine
Tropatepine
Tropicamide
Trospium chloride
Typical antipsychotics (e.g.,
chlorpromazine ,
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cyamemazine (cyamepromazine) ,
loxapine ,
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thioridazine )
Umeclidinium bromide (
+vilanterol )
WIN-2299
Xanomeline
Zamifenacin
Precursors (and
prodrugs )