diff --git a/docs/conf.py b/docs/conf.py
index 9488b636..142a3a6e 100644
--- a/docs/conf.py
+++ b/docs/conf.py
@@ -45,6 +45,8 @@
 # This pattern also affects html_static_path and html_extra_path.
 exclude_patterns = ["_build", "Thumbs.db", ".DS_Store"]
 
+nitpick_ignore = [("py:class", "Match")]
+
 
 # -- Options for HTML output -------------------------------------------------
 
diff --git a/markdown_it/parser_core.py b/markdown_it/parser_core.py
index c69a0510..98ce7aa2 100644
--- a/markdown_it/parser_core.py
+++ b/markdown_it/parser_core.py
@@ -8,7 +8,7 @@
 
 from .ruler import Ruler
 from .rules_core.state_core import StateCore
-from .rules_core import normalize, block, inline
+from .rules_core import normalize, block, inline, replace
 
 # TODO linkify, replacements, smartquotes
 _rules = [
@@ -16,7 +16,7 @@
     ["block", block],
     ["inline", inline],
     #   [ 'linkify',        require('./rules_core/linkify')        ],
-    #   [ 'replacements',   require('./rules_core/replacements')   ],
+    ["replacements", replace],
     #   [ 'smartquotes',    require('./rules_core/smartquotes')    ]
 ]
 
diff --git a/markdown_it/rules_core/__init__.py b/markdown_it/rules_core/__init__.py
index a5b8764e..72757f51 100644
--- a/markdown_it/rules_core/__init__.py
+++ b/markdown_it/rules_core/__init__.py
@@ -2,3 +2,4 @@
 from .normalize import normalize  # noqa: F401
 from .block import block  # noqa: F401
 from .inline import inline  # noqa: F401
+from .replacements import replace  # noqa: F401
diff --git a/markdown_it/rules_core/replacements.js b/markdown_it/rules_core/replacements.js
deleted file mode 100644
index 533496fa..00000000
--- a/markdown_it/rules_core/replacements.js
+++ /dev/null
@@ -1,107 +0,0 @@
-// Simple typographic replacements
-//
-// (c) (C) → ©
-// (tm) (TM) → ™
-// (r) (R) → ®
-// +- → ±
-// (p) (P) -> §
-// ... → … (also ?.... → ?.., !.... → !..)
-// ???????? → ???, !!!!! → !!!, `,,` → `,`
-// -- → –, --- → —
-//
-'use strict';
-
-// TODO:
-// - fractionals 1/2, 1/4, 3/4 -> ½, ¼, ¾
-// - miltiplication 2 x 4 -> 2 × 4
-
-var RARE_RE = /\+-|\.\.|\?\?\?\?|!!!!|,,|--/;
-
-// Workaround for phantomjs - need regex without /g flag,
-// or root check will fail every second time
-var SCOPED_ABBR_TEST_RE = /\((c|tm|r|p)\)/i;
-
-var SCOPED_ABBR_RE = /\((c|tm|r|p)\)/ig;
-var SCOPED_ABBR = {
-  c: '©',
-  r: '®',
-  p: '§',
-  tm: '™'
-};
-
-function replaceFn(match, name) {
-  return SCOPED_ABBR[name.toLowerCase()];
-}
-
-function replace_scoped(inlineTokens) {
-  var i, token, inside_autolink = 0;
-
-  for (i = inlineTokens.length - 1; i >= 0; i--) {
-    token = inlineTokens[i];
-
-    if (token.type === 'text' && !inside_autolink) {
-      token.content = token.content.replace(SCOPED_ABBR_RE, replaceFn);
-    }
-
-    if (token.type === 'link_open' && token.info === 'auto') {
-      inside_autolink--;
-    }
-
-    if (token.type === 'link_close' && token.info === 'auto') {
-      inside_autolink++;
-    }
-  }
-}
-
-function replace_rare(inlineTokens) {
-  var i, token, inside_autolink = 0;
-
-  for (i = inlineTokens.length - 1; i >= 0; i--) {
-    token = inlineTokens[i];
-
-    if (token.type === 'text' && !inside_autolink) {
-      if (RARE_RE.test(token.content)) {
-        token.content = token.content
-          .replace(/\+-/g, '±')
-          // .., ..., ....... -> …
-          // but ?..... & !..... -> ?.. & !..
-          .replace(/\.{2,}/g, '…').replace(/([?!])…/g, '$1..')
-          .replace(/([?!]){4,}/g, '$1$1$1').replace(/,{2,}/g, ',')
-          // em-dash
-          .replace(/(^|[^-])---(?=[^-]|$)/mg, '$1\u2014')
-          // en-dash
-          .replace(/(^|\s)--(?=\s|$)/mg, '$1\u2013')
-          .replace(/(^|[^-\s])--(?=[^-\s]|$)/mg, '$1\u2013');
-      }
-    }
-
-    if (token.type === 'link_open' && token.info === 'auto') {
-      inside_autolink--;
-    }
-
-    if (token.type === 'link_close' && token.info === 'auto') {
-      inside_autolink++;
-    }
-  }
-}
-
-
-module.exports = function replace(state) {
-  var blkIdx;
-
-  if (!state.md.options.typographer) { return; }
-
-  for (blkIdx = state.tokens.length - 1; blkIdx >= 0; blkIdx--) {
-
-    if (state.tokens[blkIdx].type !== 'inline') { continue; }
-
-    if (SCOPED_ABBR_TEST_RE.test(state.tokens[blkIdx].content)) {
-      replace_scoped(state.tokens[blkIdx].children);
-    }
-
-    if (RARE_RE.test(state.tokens[blkIdx].content)) {
-      replace_rare(state.tokens[blkIdx].children);
-    }
-
-  }
-};
diff --git a/markdown_it/rules_core/replacements.py b/markdown_it/rules_core/replacements.py
new file mode 100644
index 00000000..86e3c3c4
--- /dev/null
+++ b/markdown_it/rules_core/replacements.py
@@ -0,0 +1,123 @@
+"""Simple typographic replacements
+
+* ``(c)``, ``(C)`` → ©
+* ``(tm)``, ``(TM)`` → ™
+* ``(r)``, ``(R)`` → ®
+* ``(p)``, ``(P)`` → §
+* ``+-`` → ±
+* ``...`` → …
+* ``?....`` → ?..
+* ``!....`` → !..
+* ``????????`` → ???
+* ``!!!!!`` → !!!
+* ``,,,`` → ,
+* ``--`` → &ndash
+* ``---`` → &mdash
+"""
+import logging
+import re
+from typing import List, Match
+
+from .state_core import StateCore
+from ..token import Token
+
+LOGGER = logging.getLogger(__name__)
+
+# TODO:
+# - fractionals 1/2, 1/4, 3/4 -> ½, ¼, ¾
+# - miltiplication 2 x 4 -> 2 × 4
+
+RARE_RE = re.compile(r"\+-|\.\.|\?\?\?\?|!!!!|,,|--")
+
+# Workaround for phantomjs - need regex without /g flag,
+# or root check will fail every second time
+# SCOPED_ABBR_TEST_RE = r"\((c|tm|r|p)\)"
+
+SCOPED_ABBR_RE = re.compile(r"\((c|tm|r|p)\)", flags=re.IGNORECASE)
+
+PLUS_MINUS_RE = re.compile(r"\+-")
+
+ELLIPSIS_RE = re.compile(r"\.{2,}")
+
+ELLIPSIS_QUESTION_EXCLAMATION_RE = re.compile(r"([?!])…")
+
+QUESTION_EXCLAMATION_RE = re.compile(r"([?!]){4,}")
+
+COMMA_RE = re.compile(r",{2,}")
+
+EM_DASH_RE = re.compile(r"(^|[^-])---(?=[^-]|$)", flags=re.MULTILINE)
+
+EN_DASH_RE = re.compile(r"(^|\s)--(?=\s|$)", flags=re.MULTILINE)
+
+EN_DASH_INDENT_RE = re.compile(r"(^|[^-\s])--(?=[^-\s]|$)", flags=re.MULTILINE)
+
+
+SCOPED_ABBR = {"c": "©", "r": "®", "p": "§", "tm": "™"}
+
+
+def replaceFn(match: Match[str]):
+    return SCOPED_ABBR[match.group(1).lower()]
+
+
+def replace_scoped(inlineTokens: List[Token]):
+    inside_autolink = 0
+
+    for token in inlineTokens:
+        if token.type == "text" and not inside_autolink:
+            token.content = SCOPED_ABBR_RE.sub(replaceFn, token.content)
+
+        if token.type == "link_open" and token.info == "auto":
+            inside_autolink -= 1
+
+        if token.type == "link_close" and token.info == "auto":
+            inside_autolink += 1
+
+
+def replace_rare(inlineTokens: List[Token]):
+    inside_autolink = 0
+
+    for token in inlineTokens:
+        if token.type == "text" and not inside_autolink:
+            if RARE_RE.search(token.content):
+                # +- -> ±
+                token.content = PLUS_MINUS_RE.sub("±", token.content)
+
+                # .., ..., ....... -> …
+                token.content = ELLIPSIS_RE.sub("…", token.content)
+
+                # but ?..... & !..... -> ?.. & !..
+                token.content = ELLIPSIS_QUESTION_EXCLAMATION_RE.sub(
+                    "\\1..", token.content
+                )
+                token.content = QUESTION_EXCLAMATION_RE.sub("\\1\\1\\1", token.content)
+
+                # ,,  ,,,  ,,,, -> ,
+                token.content = COMMA_RE.sub(",", token.content)
+
+                # em-dash
+                token.content = EM_DASH_RE.sub("\\1\u2014", token.content)
+
+                # en-dash
+                token.content = EN_DASH_RE.sub("\\1\u2013", token.content)
+                token.content = EN_DASH_INDENT_RE.sub("\\1\u2013", token.content)
+
+        if token.type == "link_open" and token.info == "auto":
+            inside_autolink -= 1
+
+        if token.type == "link_close" and token.info == "auto":
+            inside_autolink += 1
+
+
+def replace(state: StateCore):
+    if not state.md.options.typographer:
+        return
+
+    for token in state.tokens:
+        if token.type != "inline":
+            continue
+
+        if SCOPED_ABBR_RE.search(token.content):
+            replace_scoped(token.children)
+
+        if RARE_RE.search(token.content):
+            replace_rare(token.children)
diff --git a/tests/test_api/test_main.py b/tests/test_api/test_main.py
index 575a246e..3eebdf60 100644
--- a/tests/test_api/test_main.py
+++ b/tests/test_api/test_main.py
@@ -7,7 +7,7 @@ def test_get_rules():
     md = MarkdownIt("zero")
     # print(md.get_all_rules())
     assert md.get_all_rules() == {
-        "core": ["normalize", "block", "inline"],
+        "core": ["normalize", "block", "inline", "replacements"],
         "block": [
             "table",
             "code",
diff --git a/tests/test_port/fixtures/typographer.md b/tests/test_port/fixtures/typographer.md
index e9e2bfee..39154ed0 100644
--- a/tests/test_port/fixtures/typographer.md
+++ b/tests/test_port/fixtures/typographer.md
@@ -4,6 +4,19 @@
 <p>(bad)</p>
 .
 
+copyright (Lower)
+.
+(c)
+.
+<p>©</p>
+.
+
+copyright (Upper)
+.
+(C)
+.
+<p>©</p>
+.
 
 copyright
 .
@@ -61,6 +74,14 @@ dupes
 .
 
 
+dupes-ellipsis
+.
+!... ?... ,... !!!!!!.... ????.... ,,...
+.
+<p>!.. ?.. ,… !!!.. ???.. ,…</p>
+.
+
+
 dashes
 .
 ---markdownit --- super---
diff --git a/tests/test_port/test_fixtures.py b/tests/test_port/test_fixtures.py
index 1bc74220..68c09fb7 100644
--- a/tests/test_port/test_fixtures.py
+++ b/tests/test_port/test_fixtures.py
@@ -8,6 +8,17 @@
 FIXTURE_PATH = Path(__file__).parent.joinpath("fixtures")
 
 
+@pytest.mark.parametrize(
+    "line,title,input,expected",
+    read_fixture_file(FIXTURE_PATH.joinpath("typographer.md")),
+)
+def test_typographer(line, title, input, expected):
+    md = MarkdownIt().enable("replacements")
+    md.options["typographer"] = True
+    text = md.render(input)
+    assert text.rstrip() == expected.rstrip()
+
+
 @pytest.mark.parametrize(
     "line,title,input,expected", read_fixture_file(FIXTURE_PATH.joinpath("tables.md"))
 )